Reaction Development
In synergy with the synthesis of inspirational targets possessing interesting structural and biological properties, the development of new methodologies is a consistent driving force in our lab. We pride in discovering unique reactivity harnessing transition-metal catalysis that could ultimately be applicable for the synthesis of complex natural products.
Selected Publications:
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.
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.
Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of 1,4-Diazepan-5-ones. Zachary P. Sercel, Alexander W. Sun, Brian M. Stoltz. Org. Lett. 2019, 21, 22, 9158–9161.
Palladium-catalyzed Enantioselective decarboxylative allylic alkylation of fully substituted N-acyl indole-derived enol carbonates. Eric J. Alexy, Tyler J. Fulton, Haiming Zhang, Brian M. Stoltz. Chem. Sci. 2019, 10, 5996–6000.
Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Acyclic Enol Carbonates. Eric J. Alexy, Haiming Zhang, Brian M. Stoltz. J. Am. Chem. Soc. 2018, 140, 10109–10112.
Selected Publications:
Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of 1,3-Disubstituted Isoquinolines. Alexia N. Kim, Fa Ngamnithiporn, Eric R. Welin, Martin T. Daiger, Christian U. Grünanger, Michael D. Bartberger, Scott C. Virgil, Brian M. Stoltz. ACS Catalysis, 2020, 10, 3241–3248.
Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation. J. Caleb Hethcox, Samantha E. Shockley, Brian M. Stoltz. Angew. Chem. Int. Ed. 2018, 57, 1–5.
Enantioselective Synthesis of Acylic α‐Quaternary Carboxylic Acid Derivatives via Iridium-Catalyzed Allylic Alkylation. Samantha Shockley, J. Caleb Hethcox, Brian M. Stoltz. Angew. Chem. Int. Ed. 2017, 56, 10196–10199.
Selected Publications:
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.
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.
Enantioselective Alkynylation of Trifluoromethyl Ketones Catalyzed by Cation-Binding Salen Nickel Complexes. Dongseong Park, Carina Jette, Jiyun Kim, Woo-ok Jung, Yongmin Lee, Jongwoo Park, Seungyoon Kang, Min Su Han, Brian M. Stoltz, Sukwon Hong. Angew. Chem. Int. Ed. 2019, 59, 775–779.
Nickel-Catalyzed Enantioselective Allylic Alkylation of Lactones and Lactams with Unactivated Allylic Alcohols. Fa Ngamnithiporn, Carina Jette, Shoshana Bachman, Scott C. Virgil, Brian M. Stoltz. Chem. Sci. 2018, 9, 2547–2551.
Ni-catalyzed Enantioselective C-Acylation of α-Substituted Lactams. Masaki Hayashi, Shoshana Bachman, Satoshi Hashimoto, Chad C. Eichman, Brian M. Stoltz. J. Am. Chem. Soc. 2016, 138, 8997–9000.
Selected Publications:
Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal. Carina Jette, Zhengjia Tong, Ryan Hadt, Brian M. Stoltz. Angew. Chem. Int. Ed. 2020, 59, 2033–2038.
Stereochemical Evaluation of Bis(phosphine) Copper Catalysts for the Asymmetric Alkylation of 3-Bromooxindoles with α-Arylated Malonate Esters. Chung Whan Lee, Seo-Jung Han, Scott C. Virgil, Brian M. Stoltz. Tetrahedron, 2015, 71, 3666–3670.