2024

323. Total synthesis of (–)-cylindrocyclophane A facilitated by C–H functionalization

Aaron T. Bosse, Liam R. Hunt, Camila A. Suarez, Tyler D. Casselman, Elizabeth L. Goldstein, Austin C. Wright, Hojoon Park, Scott C. Virgil, Jin-Quan Yu, Brian M. Stoltz, and Huw M. L. Davies. Science 2024, 386, 641–646.

322. Formation of All-Carbon Quaternary Centers via Enantioselective Pd-Catalyzed α-Vinylation of γ-Lactams

Farbod A. Moghadam, Jay P. Barbor, Melinda Chan, Carina Jette, Shunya Sakurai, and Brian M. Stoltz. Org. Lett. 2024, 26, 7551–7554

321. Enantioselective Nickel-Catalyzed α-Spirocyclization of Lactones

Allison M. Stanko, Melissa Ramirez, Adrian J. de Almenara, Scott C. Virgil, and Brian M. Stoltz. Org. Lett. 2024, 26, 6793–6797.

320. Systematic Route to Construct the 5–5–6 Tricyclic Core of Furanobutenolide-Derived Cembranoids and Norcembranoids

Melinda Chan, Nicholas J. Hafeman, Tyler J. Fulton, and Brian M. Stoltz. Org. Lett. 2024, 26, 6320–6323.

319. Total Synthesis of Hypersampsone M

Adrian E. Samkian, Scott C. Virgil, and Brian M. Stoltz. J. Am. Chem. Soc. 2024, 146, 18886–18891.

318. Strategies for the Development of Asymmetric and Non-Directed Petasis Reactions

Kevin J. Gonzalez, Chloe Cerione, and Brian M. Stoltz. Chem. Eur. J. 2024, e202401936.

317. Evolution of a Synthetic Strategy toward the Syntheses of Bis-tetrahydroisoquinoline Alkaloids

Aurapat Ngamnithiporn, Eric R. Welin, Gerit Pototschnig, and Brian M. Stoltz. Acc. Chem. Res. 2024, 57, 1870–1884.

316. Molecular Dynamics Investigations of Dienolate [4 + 2] Reactions

Peng-Jui Chen, Alexander Q. Cusumano, Kaylin N. Flesch, Christian Santiago Strong, William A. Goddard III, and Brian M. Stoltz. J. Am. Chem. Soc. 2024, 146, 12758–12765.

315. Convenient access to a strained bicyclic enone: A concise and improved formal synthesis of ineleganolide

Benjamin M. Gross and Brian M. Stoltz. Tetrahedron Lett. 2024, 140, 155011

[Invited contribution in honor of Professor Thomas Maimone, recipient of the 2024 Tetrahedron Young Investigator Award.]

314. Divergent Total Syntheses of Pyrroloiminoquinone Alkaloids Enabled by the Development of a Larock/Buchwald–Hartwig Annulation/Cyclization

Samir P. Rezgui, Jonathan Farhi, Hao Yu, Zachary P. Sercel, Scott C. Virgil, and Brian M. Stoltz. Chem. Sci. 2024, 15, 12284–12290.

[This article is part of the themed collection: 2024 Chemical Science HOT Article Collection]

313. Enantioselective Total Synthesis of (–)-Hunterine A Enabled by a Desymmetrization/Rearrangement Strategy

Elliot F. Hicks, Kengo Inoue, Brian M. Stoltz. J. Am. Chem. Soc. 2024, 146, 4340-4345.

312. Low Part-Per-Trillion, Humidity Resistant Detection of Nitric Oxide Using Microtoroid Optical Resonators

Yinchao Xu, Allison Stanko, Chloe Cerione, Trevor Lohrey, Euan McLeod, Brian Stoltz, Judith Su. ACS Appl. Mater. Interfaces 2024, 16, 5120–5128.

2023

311. Particle-phase accretion forms dimer esters in pinene secondary organic aerosol

Christopher M. Kenseth, Nicholas J. Hafeman, Samir P. Rezgui, Jing Chen, Yuanlong Huang, Nathan F. Dalleska, Henrik G. Kjaergaard, Brian M. Stoltz, John H. Seinfeld, and Paul O. Wennberg. Science. 2023, 382, 787-792.

310. Total Synthesis of Aleutianamine

Hao Yu, Zachary Sercel, Samir Rezgui, Jonathan Farhi, Scott Virgil, and Brian Stoltz. J. Am. Chem. Soc. 2023, 145, 47, 25533–25537.

309. Origins of Enhanced Enantioselectivity in the Pd-Catalyzed Decarboxylative Allylic Alkylation of N-Benzoyl Lactams

Alexander Q. Cusumano, Tianyi Zhang , William A. Goddard III and Brian M. Stoltz. Catalysts. 2023, 13, 1258.

308. Enantioselective 1,3-Dipolar Cycloadditions of α‑Methylene Lactams to Construct Spirocycles

Yuji Nishiura, Kevin J. Gonzalez, Alexander Q. Cusumano and Brian M. Stoltz. Org. Lett. 2023, 25, 6469–6473.

307. Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Lactams: Enantioselective Construction of All-Carbon Quaternary Stereocenters in Saturated Nitrogen-Containing Heterocycles

Tianyi Zhang, Yuji Nishiura, Alexander Q. Cusumano and Brian M. Stoltz. Org. Lett. 2023, 25, 6479–6484.

306. Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020)

Alexia N. Kim, Aurapat Ngamnithiporn, Emily Du, and Brian M. Stoltz. Chem. Rev. 2023, 123, 9447–9496.

305. Development of a Nickel-Catalyzed N–N Coupling for the Synthesis of Hydrazides

Jay P. Barbor, Vaishnavi N. Nair, Kimberly R. Sharp, Trevor D. Lohrey, Sara E. Dibrell, Tejas K. Shah, Martin J. Walsh, Sarah E. Reisman, and Brian M. Stoltz. J. Am. Chem. Soc. 2023, 145, 15071–15077.

304. Tandem Dearomatization/Enantioselective Allylic Alkylation of Pyridines

Steffen Greßies, Lars Süße, Tyler Casselman, and Brian M. Stoltz. J. Am. Chem. Soc. 2023, 145, 11907-11913.

303. Divergent Catalysis: Catalytic Asymmetric [4+2] Cycloaddition of Palladium Enolates

Kaylin N. Flesch*, Alexander Q. Cusumano*, Peng-Jui Chen, Christian Santiago Strong, Stephen R. Sardini, Yun E. Du, Michael D. Bartberger, William A. Goddard III, Brian M. Stoltz. J. Am. Chem. Soc. 2023, 145, 11301–11310. [* denotes equal contribution]

302. Total Synthesis of Strempeliopidine and Non-Natural Stereoisomers through a Convergent Petasis Borono–Mannich Reaction

Alexander W. Rand, Kevin J. Gonzalez, Christopher E. Reimann, Scott C. Virgil, Brian M. Stoltz. J. Am. Chem. Soc. 2023, 145, 7278–7287. [highlighted in OPR&D]

301. Total synthesis of (−)-scabrolide A and (−)-yonarolide

Nicholas J. Hafeman, Steven A. Loskot, Christopher E. Reimann, Beau P. Pritchett, Scott C. Virgil, Brian M. Stoltz. Chem. Sci., 2023, 14, 4745–4758.

300. Accretion Product Formation in the Self-Reaction of Ethene-Derived Hydroxy Peroxy Radicals

Sara Edinger Murphy , John D. Crounse , Kristian H. Møller , Samir Rezgui , Nicholas J Hafeman , James Park , Henrik Kjaergaard , Brian M. Stoltz and Paul O Wennberg. Environ. Sci.: Atmos., 2023, 3, 882–893.

299. A Convergent Total Synthesis of (+)-Ineleganolide

Benjamin M. Gross, Seo-Jung Han, Scott C. Virgil, Brian M. Stoltz. J. Am. Chem. Soc., 2023, 145, 7763–7767.

298. Development of a Non-Directed Petasis-Type Reaction by an Aromaticity-Disrupting Strategy

Kevin J. Gonzalez, Alexander W. Rand, Brian M. Stoltz. Angew. Chem. Int. Ed., 2023, 62, e202218921.

297. What is a cross-coupling? An argument for a universal definition

Christopher E. Reimann, Kelly E. Kim, Alexander W. Rand, Farbod A. Moghadam, and Brian M. Stoltz. Tetrahedron., 2023, 130, 133176.

2022

296. Asymmetric Total Synthesis of Havellockate

Nicholas J. Hafeman*, Melinda Chan*, Tyler J. Fulton, Eric J. Alexy, Steven A. Loskot, Scott. C. Virgil, and Brian M. Stoltz. J. Am. Chem. Soc., 2022, 144, 20232-20236. [* denotes equal contribution]

295. Investigations of an Unexpected [2+2] Photocycloaddition in the Synthesis of (−)-Scabrolide A from Quantum Mechanics Calculations

Tianyi Zhang*, Alexander Q. Cusumano*, Nicholas J. Hafeman, Steven A. Loskot, Christopher E. Reimann, Scott C. Virgil, William A. Goddard III, and Brian M. Stoltz. J. Org. Chem., 2022, 87, 14115-14124. [* denotes equal contribution]

294. Synthesis of enantioenriched 2,2-disubstituted pyrrolidines via sequential asymmetric allylic alkylation and ring contraction

Elizabeth L. Goldstein, Hirokazu Takada, Yuji Sumii, Katsuaki Baba, Brian M. Stoltz. Tetrahedron 2022, 132940.

293. Part-per-Trillion Trace Selective Gas Detection Using Frequency Locked Whispering-Gallery Mode Microtoroids

Cheng Li, Trevor Lohrey, Phuong-Diem Nguyen, Zhouyang Min, Yisha Tang, Chang Ge, Zachary P. Sercel, Euan McLeod, Brian M. Stoltz, Judith Su. ACS Appl. Mater. Interfaces 2022, 14, 42430–42440.

292. Ir-Catalyzed Asymmetric Allylic Alkylation of Dialkyl Malonates Enabling the Construction of Enantioenriched All-Carbon Quaternary Centers

Farbod A. Moghadam,* Elliot F. Hicks,* Zachary P Sercel, Alexander Q. Cusumano, Michael D. Bartberger, Brian M. Stoltz. J. Am. Chem. Soc. 2022, 144, 7983–7987

[* denotes equal contribution]

291. Iridium-Catalyzed Asymmetric trans-Selective Hydrogenation of 1,3-Disubstituted Isoquinolines

Alexia N. Kim, Aurapat Ngamnithiporn, Michael D. Bartberger, Brian M. Stoltz. Chem. Sci. 2022, 13, 3227-3232.

[Highlighted in Synfacts]

290. Isotope effects at the origin of life: Fingerprints of the Strecker synthesis

L. Chimiak, J. Eiler, A. Sessions, C. Blumenfeld, M. Klatte, Brian M. Stoltz. Geochimica et Cosmochimica Acta 2022, 321, 78–98.

289. Some Unusual Transformations of a Highly Reactive α-Bromocaranone

Adrian E. Samkian, Zachary P. Sercel, Scott C. Virgil, Brian M. Stoltz. Tetrahedron Lett. 2022, 89, 153496.

2021

288. Late-Stage Diversification: A Motivating Force in Organic Synthesis

Kelly E. Kim, Alexia N. Kim, Carter J. McCormick, Brian M. Stoltz. J. Am. Chem. Soc. 2021, 143, 16890–1690.

287. Synthesis of Enantioenriched gem-Disubstituted 4-Imidazolidinones by Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

Zachary P. Sercel, Alexander W. Sun, Brian M. Stoltz Org. Lett. 2021, 23, 6348-6351.

286. Identifying the Imperative Role of Metal–Olefin Interactions in Catalytic C–O Reductive Elimination from Nickel(II)

Trevor D. Lohrey, Alexander Q. Cusumano, William A. Goddard III, Brian M. Stoltz ACS Catal. 2021, 11, 10208–10222.

285. Synthetic strategy toward ineleganolide: A cautionary tale

Alexander Q. Cusumano, K. N. Houk, Brian M. Stoltz Tetrahedron, 2021, 93, 132289.

[Invited submission in honor of Prof. Dale L. Boger]

284. The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16’-epi-Leucophyllidine

Christopher E. Reimann, Aurapat Ngamnithiporn, Kohei Hayashida, Daisuke Saito, Katerina M. Korch, Brian M. Stoltz Angew. Chem. Int. Ed. 2021, 60, 17957-17962.

283. Preparation of (S)-tert-ButylPyOx and Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids

Stephen R. Sardini, Brian M. Stoltz Org. Synth. 2021, 98, 117–130.

282. Discovery of novel modulators for the PPARα (peroxisome proliferator activated receptor α): Potential therapies for nonalcoholic fatty liver disease

Donna D. Yu, Gregg Van Citters, Hongzhi Li, Brian M. Stoltz, and Barry M. Forman Bioorg. Med. Chem. 2021, 41, 116193.

281. A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement

Seo-Jung Han, Marchello A. Cavitt, Brian M. Stoltz Org. Lett. 2021, 23, 3300–3303.

280. A covalent p97/VCP ATPase inhibitor can overcome resistance to CB-5083 and NMS-873 in colorectal cancer cells

Gang Zhang, Shan Li, Feng Wang, Amanda C. Jones, Alexander F.G. Goldberg, Benjamin Lin, Scott Virgil, Brian M. Stoltz, Raymond Deshaies, Tsui-en Chou Eur. J. Med. Chem. 2021, 213, 113148.

279. Enantioselective Formation of Quaternary Centers by Allylic Alkylation with First-Row Transition-Metal Catalysts

Lars Süsse and Brian M. Stoltz Chem. Rev. 2021, 121, 4084–4099.

2020

278. Recent Advances in Homogeneous Catalysts for the Asymmetric Hydrogenation of Heteroarenes.

Alexia N. Kim and Brian M. Stoltz ACS Catal. 2020, 10, 13834–13851.

277. Global Diastereoconvergence in the Ireland–Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids

Tyler J. Fulton,* Alexander Q. Cusumano,* Eric J. Alexy, Yun Emily Du, Haiming Zhang, Ken N. Houk, and Brian M. Stoltz J. Am. Chem. Soc. 2020, 142, 21938–21947. (* Equal Contribution)

[Highlighted in Synfacts]

276. The Transition Metal Catalyzed [π2s + π2s + σ2s + σ2s] Pericyclic Reaction: Woodward–Hoffmann Rules, Aromaticity, and Electron Flow

Alexander Q. Cusumano, William A. Goddard III, and Brian M. Stoltz J. Am. Chem. Soc. 2020, 142, 19033–19039.

[Featured article in C&EN News: “Chemists shine light on new way to think about reductive elimination” ]

[Featured in JACS Spotlights: “Follow the Yellow Brick Density,” J. Am. Chem. Soc. 2020, 142, 18999–19000.]

275. Enantioselective Synthesis of Highly Oxygenated Acyclic Quaternary Center-Containing Building Blocks via Palladium-Catalyzed Decarboxylative Allylic Alkylation of Cyclic Siloxyketones

Aurapat Ngamnithiporn, Toshihiko Iwayama, Michael D. Bartberger, and Brian M. Stoltz Chem. Sci. 2020, 11, 11068–11071.

274. Efficient Synthesis of Geminal-Dialkyl Dienes for Olefin Metathesis Polymerization

William J. Wolf,* Jiaming Li,* Simon C. Jones, Brian M. Stoltz, and Robert H. Grubbs Macromolecules 2020, 53, 7803–7809. [*denotes equal contribution]

273. Synthesis of Carboxylic Acid and Dimer Ester Surrogates to Constrain the Abundance and Distribution of Molecular Products in α-Pinene and β-Pinene Secondary Organic Aerosol

Christopher M. Kenseth, Nicholas J. Hafeman, Yuanlong Huang, Nathan F. Dalleska, Brian M. Stoltz, and John H. Seinfeld Enviorn. Sci. Technol. 2020, 54, 12829–12839.

272. Reaction Mechanism, Origins of Enantioselectivity, and Reactivity Trends in Asymmetric Allylic Alkylation: A Comprehensive Quantum Mechanics Investigation of a C(sp3)–C(sp3) Cross-Coupling.

Alexander Q. Cusumano, William A. Goddard III, and Brian M. Stoltz J. Am. Chem. Soc. 2020, 142, 13917–13933.

271. Catalytic Enantioselective Synthesis of Carbocyclic and Heterocyclic Spiranes via a Decarboxylative Aldol Cyclization

Kazato Inanaga,* Marco Wollenburg,* Shoshana Bachman, Nicholas J. Hafeman, and Brian M. Stoltz Chem. Sci. 2020, 11, 7390–7395. (* Equal Contribution)

270. Probing Trends in Enantioinduction via Substrate Design: Palladium-Catalyzed Decarboxylative Allylic Alkylation of α-Enaminones

Douglas C. Duquette, Alexander Q. Cusumano, Louise Lefoulon, Jared T. Moore, and Brian M. Stoltz Org. Lett. 2020, 22, 4966–4969.

269. Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones

Remi Lavernhe, Eric J. Alexy, Haiming Zhang, and Brian M. Stoltz Org. Lett. 2020, 22, 4272–4275.

268. The Total Synthesis of (–)-Scabrolide A

Nicholas J. Hafeman, Steven A. Loskot, Chris E. Reimann, Beau P. Pritchett, Scott C. Virgil, and Brian M. Stoltz J. Am. Chem. Soc. 2020. 142, 8585–8590.

[Featured on Organic Chemistry Portal issue on Diels–Alder Reactions in Synthesis: D. F. Taber, Org. Chem. Highlights 2020, November 30.]

267. Catalytic Enantioselective Synthesis of Tetrasubstituted Chromanones via Palladium-Catalyzed Asymmetric Conjugate Arylation using Chiral Pyridine-Dihydroisoquinoline Ligands

Doohyun Baek, Huijeong Ryu, Ji Yeon Ryu, Junseong Lee, Brian M. Stoltz, and Sukwon Hong Chem. Sci. 2020, 11, 4602–4607.

266. Enantioselective Total Synthesis of (–)-Myrifabral A and B

Tyler J. Fulton, Anthony Chen, Michael D. Bartberger, and Brian M. Stoltz Chem. Sci. 2020, 11, 10802–10806.

265. Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of 1,3-Disubstituted Isoquinolines

Alexia N. Kim, Aurapat Ngamnithiporn, Eric R. Welin, Martin Daiger, Christian Grünanger, Michael D. Bartberger, Scott C. Virgil, and Brian M. Stoltz. ACS Catal. 2020, 10, 3241–3248.

2019

264. Enantioselective Synthesis of 15-Deoxy-Δ12,14-Prostaglandin J2

Jiaming Li, Brian M. Stoltz, and Robert H. Grubbs. Org. Lett. 2019, 21, 10139−10142.

263. Palladium‐Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Protected Benzoin‐Derived Enol Carbonates

Rémi Lavernhe, Eric J. Alexy, Haiming Zhang, Brian M. Stoltz. Adv. Synth. Catal. 2020, 362, 344–347. 

262. Progress toward the Enantioselective Synthesis of Curcusones A–D via a Divinylcyclopropane Rearrangement Strategy

Austin C. Wright, Chung Whan Lee, and Brian M. Stoltz. Org. Lett. 2019, 21, 9658–9662.

261.  Cu‐Catalyzed Enantioselective Allylic Alkylation with a γ‐Butyrolactone‐Derived Silyl Ketene Acetal

Carina Jette, Zhengjia Tong, Ryan Hadt, and Brian Stoltz. Angew. Chem. Int. Ed. 2020, 59, 2023–2038.

260.  Enantioselective Alkynylation of Trifluoromethyl Ketones Catalyzed by Cation-Binding Salen Nickel Complexes

Dongseong Park, Carina I. Jette, Jiyun Kim, Woo-ok Jung, Yongmin Lee, Jongwoo Park, Seungyoon Kang, Min Su Han, Brian Stoltz, and Sukwon Hong. Angew. Chem. Int. Ed. 2020, 7, 775–779.

259.  Synthesis of non-natural cyanthiwigin–gagunin hybrids through late-stage diversification of the cyanthiwigin natural product core

Kelly E. Kim, Yuka Sakazaki, and Brian M. Stoltz. Tetrahedron 2019, In Press.

258.  Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of 1,4-Diazepan-5-ones

Zachary P. Sercel,* Alexander W. Sun,* and Brian M. Stoltz. Org. Lett. 2019, 21, 9158–9161.  (* Equal Contribution)

257.  Stereospecific Overman Rearrangement of Substituted Cyclic Vinyl Bromides: Access to Fully Substituted α-Amino Ketones

Álvaro Velasco-Rubio, Eric J. Alexy, Makoto Yoritate, Austin C. Wright, and Brian M. Stoltz. Org. Lett. 2019, 21, 8962–8965.

256.  Modularity: Adding New Dimensions to Total Synthesis

Alexander W. Sun,* Sebastian Lackner,* and Brian M. Stoltz. Trends in Chemistry 2019, 1, 630–643. (* Equal Contribution)

255.  Enantioselective Construction of the Tricyclic Core of Curcusones A–D via a Cross-electrophile Coupling Approach

Austin C. Wright and Brian M. Stoltz. Chem. Sci. 2019, 10, 10562-10565.

254.  A Small-scale Procedure for Acid-catalyzed Ketal Formation

Austin C. Wright, Yun Emily Du, and Brian M. Stoltz. J. Org. Chem. 2019, 84, 11258–11260.

253.  Incorporation of a chiral gem-disubstituted nitrogen heterocycle yields an oxazolidinone antibiotic with reduced mitochondrial toxicity

Alexander W. Sun, Philip L. Bulterys, Michael D. Bartberger, Peter A. Jorth, Brendan M. O'Boyle, Scott C. Virgil, Jeff F. Miller, and Brian M. Stoltz. Bioorg. Med. Chem. Lett. 2019, 29, 2686–2689.

252.  Unified Enantioselective, Convergent Synthetic Approach toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Synthesis of a Series of Ineleganoloids by Oxidation-State Manipulation of the Carbocyclic Core

Robert A. Craig, Russell C. Smith, Jennifer L. Roizen, Amanda C. Jones, Scott C. Virgil, and Brian M. Stoltz. J. Org. Chem. 2019, 84, 7722–7746.

251.  Palladium-catalyzed α,β-dehydrogenation of acyclic ester equivalents promoted by a novel electron deficient phosphinooxazoline ligand

Tyler J. Fulton, Brenda Wu, Eric J. Alexy, Haiming Zhang, and Brian M. Stoltz. Tetrahedron 2019, 75, 4104–4109.

Invited submission in honor of Professor John F. Hartwig on his receipt of the Tetrahedron Prize

250.  Palladium-catalyzed enantioselective decarboxylative allylic alkylation of fully substituted N-acyl indole-derived enol carbonates

Eric J. Alexy, Tyler J. Fulton, Haiming Zhang, and Brian M. Stoltz. Chem. Sci. 2019, 10, 5996–6000.

249.  Characterization of reactive organometallic species via MicroED

Christopher Jones, Matthew Asay, Lee Joon Kim, Jack Kleinsasser, Ambarneil Saha, Tyler J. Fulton, Kevin Berkley, Duilio Cascio, Andrey Malyutin, Matthew Conley, Brian M. Stoltz, Vincent LaVallo, Jose A. Rodriguez, Hosea Nelson. ACS Cent. Sci. 2019, 5, 1507–1513.

248.  Cycloadditions of Oxacyclic Allenes and a Catalytic Asymmetric Entryway to Enantioenriched Cyclic Allenes

Michael M. Yamano, Rachel R. Knapp, Aurapat Ngamnithiporn, Melissa Ramirez, Kendall N. Houk, Brian M. Stoltz, Neil K. Garg. Angew. Chem. Int. Ed.  2019, 58, 5653–5657.

247.  Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2-(2-acetylphenyl)acetate

Austin C. Wright and Brian M. Stoltz. Org. Synth. 2019, 96, 80–97.

246.  An unexpected Ireland–Claisen rearrangement cascade during the synthesis of the tricyclic core of Curcusone C: Mechanistic elucidation by trial-and-error and automatic artificial force-induced reaction (AFIR) computations

Chung Whan Lee, Buck L. H. Taylor, Galina P. Petrova, Ashay Patel, Keiji Morokuma, K. N. Houk, and Brian M. Stoltz. J. Am. Chem. Soc.  2019, 141, 6995–7004.

245.  Development of a catalytic enantioselective synthesis of the guanacastepene and heptemerone tricyclic core

Andrew M. Harned and Brian M. Stoltz. Tetrahedron 2019, 75, 3166–3177.

[This paper is dedicated to Professor Ryan A. Shenvi on receipt of the Tetrahedron Young Investigator Award.]

244.  Palladium‐Catalyzed Construction of Quaternary Stereocenters by Enantioselective Arylation of γ‐Lactams with Aryl Chlorides and Bromides

Carina Jette, Irina Geibel, Shoshana Bachman, Masaki Hayashi, Shunya Sakurai, Hideki Shimizu, Jeremy B. Morgan, and Brian Stoltz. Angew. Chem. Int. Ed.  2019, 58, 4297–4301.

243.  Atroposelective Synthesis of PINAP via Dynamic Kinetic Asymmetric Transformation

Seo-Jung Han, Vikram Bhat, Brian M. Stoltz, and Scott C. Virgil. Adv. Synth. Catal.  2019, 361, 441–444.

242.  Intramolecular Hydrogen Shift Chemistry of Hydroperoxy-Substituted Peroxy Radicals 

Eric Praske, Rasmus V. Otkjær, John D. Crounse, J. Caleb Hethcox, Brian M. Stoltz, Henrik G. Kjaergaard, and Paul O. Wennberg. J. Phys. Chem. A  2019, 123, 590–600.

241.  Concise total syntheses of (–)-jorunnamycin A and (–)-jorumycin enabled by asymmetric catalysis 

Eric R. Welin, Aurapat Ngamnithiporn, Max Klatte, Guillaume Lapointe, Gerit M. Pototschnig, Martina S. J. McDermott, Dylan Conklin, Christopher D. Gilmore, Pamela M. Tadross, Christopher K. Haley, Kenji Negoro, Emil Glibstrup, Christian U. Grünanger, Kevin M. Allan, Scott C. Virgil, Dennis J. Slamon, and Brian M. Stoltz. Science 2019, 363, 270–275.

240.  Concise Syntheses of Δ12-Prostaglandin J Natural Products via Stereoretentive Metathesis

Jiaming Li, Tonia S. Ahmed, Chen Xu, Brian M. Stoltz, and Robert H. Grubbs J. Am. Chem. Soc. 2019, 141, 1, 154–158.

2018

239.  Discussion Addendum for: Preparation of (S)-tert-ButylPHOX and (S)-2-Allyl-2-Methylcyclohexanone"

Alexander W. Sun and Brian M. Stoltz Org. Synth. 2018, 95, 439-454.

238.  The CryoEM Method MicroED as a Powerful Tool for Small Molecule Structure Determination

Christopher G. Jones*, Michael W. Martynowycz*, Johan Hattne, Tyler J. Fulton, Brian M. Stoltz, Jose A. Rodriguez, Hosea M. Nelson, and Tamir Gonen. ACS Cent. Sci. 2018, 4, 1587–1592. [*denotes equal contribution]

237.  Enantioselective synthesis of gem-disubstituted N-Boc diazaheterocycles via decarboxylative asymmetric allylic alkylation

Alexander W. Sun*, Stephan N. Hess* and Brian M. Stoltz. Chem. Sci. 2018, 10, 788–792. [*denotes equal contribution]

236.  Catalyst-Controlled Selective Functionalization of Unactivated C–H Bonds in the Presence of Electronically Activated C–H Bonds

Wenbin Liu, Zhi Ren, Aaron T. Bosse, Kuangbiao Liao, Elizabeth L. Goldstein, John Bacsa, Djamaladdin G. Musaev, Brian M. Stoltz, and Huw M. L. Davies. J. Am. Chem. Soc. 2018, 140, 12247–12255.

235.  Palladium-Catalyzed Enantioselective Csp3–Csp3 Cross-Coupling for the Synthesis of (Poly)fluorinated Chiral Building Blocks

Yanhui Lu, Elizabeth L. Goldstein, and Brian M. Stoltz. Org. Lett. 2018, 20, 5657–5660.

234.  Synergistic O3 + OH oxidation pathway to extremely low-volatility dimers revealed in β-pinene secondary organic aerosol

Christopher M. Kenseth, Yuanlong Huang, Ran Zhao, Nathan F. Dalleska, J. Caleb Hethcox, Brian M. Stoltz, and John H. Seinfeld. Proc. Natl. Acad. Sci. USA 2018, 115, 8301–8306.

233.  Intermolecular Stereoselective Iridium-Catalyzed Allylic Alkylation: An Evolutionary Account

Samantha E. Shockley, J. Caleb Hethcox, and Brian M. Stoltz. Synlett 2018, 29, A–L.

232.  General and Practical Potassium Methoxide/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Arylhalides

Xin Wang, Ming-Hui Zhu, David P Schuman, Dayou Zhong, Wen-Yan Wang, Lin-Yang Wu, Wei Liu, Brian M. Stoltz, and Wen-Bo Liu. J. Am. Chem. Soc. 2018, 140, 10970–10974.

231.  Catalytic Enantioselective Synthesis of Acyclic Quaternary Centers: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Acyclic Enol Carbonates

Eric J. Alexy, Haiming Zhang, and Brian M. Stoltz. J. Am. Chem. Soc. 2018, 140, 10109–10112.

230.  Short Enantioselective Formal Synthesis of (–)-Platencin

Christian Defieber, Justin T. Mohr , Gennadii A. Grabovyi, Brian M. Stoltz. Synthesis 2018, 50, A–J

229.  Total Synthesis of the Norhasubanan Alkaloid Stephadiamine

Nina Hartrampf, Nils Winter, Gabriele Pupo, Brian M. Stoltz, and Dirk Trauner. J. Am. Chem. Soc. 2018, 140, 8675–8680.

[Featured in SynFacts]

228.  Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation

J. Caleb Hethcox, Samantha E. Shockley, and Brian M. Stoltz. Angew. Chem. Int. Ed. 2018, 57, 1–5.

[Featured in SynFacts]

227.  Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids

Beau P. Pritchett and Brian M. Stoltz. Nat. Prod. Rep. 2018, 35, 559-574.

226.  Development of a Unified Enantioselective, Convergent Synthetic Approach Toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Asymmetric Formation of the Polycyclic Norditerpenoid Carbocyclic Core by Tandem Annulation Cascade

Robert A. Craig, II, Russell C. Smith, Jennifer L. Roizen, Amanda C. Jones, Scott C. Virgil, and Brian M. Stoltz. J. Org. Chem. 2018, 83, 3467–3485.

225.  Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols

Aurapat Ngamnithiporn, Carina I. Jette, Shoshana Bachman, Scott C. Virgil, and Brian M. Stoltz. Chem. Sci. 2018, 9, 2547–2551.

224.  Cyanthiwigin Natural Product Core as a Complex Molecular Scaffold for Comparative Late-Stage C–H Functionalization Studies

Kelly E. Kim, Ashley M. Adams, Nicholas D. Chiappini, J. Du Bois, and Brian M. Stoltz J. Org. Chem. 2018, 83, 3023–3033.

223.  Wolff/Cope Approach to the AB Ring of the Sesterterpenoid Variecolin

Michael R Krout, Christopher Edwin Henry, Thomas Jensen, Kun-Liang (Phil) Wu, Scott C Virgil, and Brian M. Stoltz J. Org. Chem. 2018, 83, 6995–7009.