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 Created by Oleksandr Zhurakovskyi

Caltech Center for Catalysis and Chemical Synthesis Center for Selective CH Functionalization Resnick Sustainability Institute at Caltech

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4.2014

• Our most recent publication, "Development of (Trimethylsilyl)ethyl Ester Protected Enolates and Applications in Palladium-Catalyzed Enantioselective Allylic Alkylation: Intermolecular Cross-Coupling of Functionalized Electrophiles" has been published in Org. Lett. You can find it on our publications page.

• Our recent publication, "Palladium-catalyzed decarboxylative allylic alkylation of diastereomeric β-ketoesters," has been published in Tetrahedron You can find it on our publications page.

3.2014

• Our most recent publication, "Stereoselective Lewis Acid Mediated (3+2) Cycloadditions of N-H- and N-Sulfonylaziridines with Heterocumulenes" has been published in Chem.—Eur. J. You can find it on our publications page.

2.2014

• Caltech was recently the subject of two Times Higher Education features. Check out Caltech's secret to success and the 10 reasons why Caltech was ranked the world's number one university.

• Our latest collaborative review, "Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements," has been published in Angew. Chem. Int. Ed. and Angew. Chem. You can find it on our publications page.

• Our collaboration with the Seinfeld and Wennberg groups, "Gas Phase Production and Loss of Isoprene Epoxydiols," has been published in J. Phys. Chem. A You can find it on our publications page.

1.2014

• Our most recent collaboration with the Grubbs group, "Palladium-Catalyzed Decarbonylative Dehydration of Fatty Acids for the Production of Linear Alpha Olefins," has been published in Adv. Synth. Catal. You can find it on our publications page.

• Our partnership with Bejanmin Franklin Magnet School was featured on the Center for C–H Activation Website!

• Our recent publication, "Enantio-, Diastereo- and Regioselective Iridium-Catalyzed Asymmetric Allylic Alkylation of Acyclic β-Ketoesters," was Synfact of the Month!

• Our recent publication, "Asymmetric Synthesis of QUINAP via Dynamic Kinetic Resolution," has been featured in Synfacts!

• Our recent publication, "Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters via Ir-Catalyzed Regio‑, Diastereo‑, and Enantioselective Allylic Alkylation and Applications in Sequential Pd Catalysis," has been featured in Synfacts!

12.2013

• Our most recent publication, "A Unified Approach to the Daucane and Sphenolobane Bicyclo[5.3.0]decane Core: Enantioselective Total Syntheses of Daucene, Daucenal, Epoxydaucenal B, and 14-p-Anisoyloxydauc-4,8-diene" has been published in Chem.—Eur. J. You can find it on our publications page.

• Congratulations to former Stoltz Group visiting scholar Kei Murakami for his appointment as Assistant Professor at Kyoto University in the group of Profs. Atsuhiro Osuka and Hideki Yorimitsu.

10.2013

• Our most recent publication, "Enantio-, Diastereo- and Regioselective Iridium-Catalyzed Asymmetric Allylic Alkylation of Acyclic β-Ketoesters" has been published in J. Am. Chem. Soc. You can find it on our publications page.

• Our latest collaboration with the Caltech Center for Catalysis and Chemical Synthesis, "Asymmetric Synthesis of QUINAP via Dynamic Kinetic Resolution," can be found on the J. Am. Chem. Soc. Just Accepted Manuscripts page. You can find a link on our publications page.

9.2013

• Our latest collaboration with the Prasadarao group at Children's Hospital Los Angeles, "Angiotensin receptor I - A novel target for preventing neonatal meningitis in mice by Escherichia coli K1," can be found on the J. Infect. Dis. Accepted Manuscripts page. You can find a link on our publications page.

• Our latest collaboration with the Houk group at UCLA, "Mechanism and Enantioselectivity in Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β-Substituted Cyclic Enones: Insights from Computation and Experiment" can be found on the J. Am. Chem. Soc. Just Accepted Manuscripts page. You can find a link on our publications page.

8.2013

• Our most recent publication, "A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyOx) ligand" has been published in Beilstein J. Org. Chem. You can find it on our publications page.

7.2013

• Please check out the Dow Lab Safety Academy for useful information on safe practices in the laboratory. There is also a link up on our links page.

• Our most recent publication, "Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters via Ir-Catalyzed Regio‑, Diastereo‑, and Enantioselective Allylic Alkylation and Applications in Sequential Pd Catalysis" has been published in J. Am. Chem. Soc. You can find it on our publications page.

• Our most recent publication, "Enantioselective Synthesis of the 5–6–7 Carbocyclic Core of the Gagunin Diterpenoids" has been published in Org. Lett. You can find it on our publications page.

6.2013

• Our most recent collaboration with Caltech professor Niles Pierce, "Selective Nucleic Acid Capture with Shielded Covalent Probes" has been published in J. Am. Chem. Soc. You can find it on our publications page.

5.2013

• Our most recent publication, "Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation" has been published in Angew. Chem. Int. Ed. You can find it on our publications page.

• Our most recent publication, "Total Syntheses of (−)-Transtaganolide A, (+)-Transtaganolide B, (+)-Transtaganolide C, and (−)-Transtaganolide D and Biosynthetic Implications" has been published in Angew. Chem. Int. Ed. You can find it on our publications page.

3.2013

• Our most recent publication, "The Construction of All-Carbon Quaternary Stereocenters by Use of Pd-Catalyzed Asymmetric Allylic Alkylation Reactions in Total Synthesis" has been published in Eur. J. Org. Chem You can find it on our publications page.

• Our most recent publication, "Development of a palladium-catalyzed decarboxylative cross-coupling of (2-azaaryl)carboxylates with aryl halides" has been published in Tetrahedron You can find it on our publications page.

2.2013

• Our most recent publication, "Expanding Insight into Asymmetric Palladium-Catalyzed Allylic Alkylation of N-Heterocyclic Molecules and Cyclic Ketones" has been published in Chem.—Eur. J. You can find it on our publications page.

• Our most recent publication, "Use of a palladium(II)-catalyzed oxidative kinetic resolution in synthetic efforts toward bielschowskysin" has been published in Tetrahedron You can find it on our publications page.

12.2012

• Our most recent publication, "Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Heterocyclic Acceptors" has been published in Chem.—Eur. J. You can find it on our publications page.

11.2012

• Our most recent publication, "Rapid and Convergent Synthesis of a 2,4’-Linked Tri-oxazole in an Approach to Poly-oxazoles" has been published in Heterocycles. You can find it on our publications page.

• Our most recent publication, "The Reaction Mechanism of the Enantioselective Tsuji Allylation: Inner-Sphere and Outer-Sphere Pathways, Internal Rearrangements, and Asymmetric C–C Bond Formation" has been published in J. Am. Chem. Soc. You can find it at our publications page.

• Our most recent publication, "Enantioselective Synthesis of a Hydroxymethyl-cis-1,3-cyclopentenediol Building Block" has been published in Org. Lett. You can find it at our publications page.

10.2012

• Our most recent publication, "Lewis Acid Mediated (3 + 2) Cycloadditions of Donor–Acceptor Cyclopropanes with Heterocumulenes" has been published in Org. Lett. You can find it at our publications page.

9.2012

• Pam and Chris's Chemistry themed wedding reception was covered in a recent C&E News blog post.

8.2012

• Welcome to our newest graduate student, Katerina Korch from Juniata College!

• Our recent publication, "Enantioselective Total Synthesis of the Reported Structures of (–)-9-epi-Presilphiperfolan-1-ol and (–)-Presilphiperfolan-1-ol: Structural Confirmation and Reassignment and Biosynthetic Insights." has been published in Angew. Chem. Int. Ed. You can find it at our publications page.

• Our recent publication, ""A C–N Insertion of β-Lactam to Benzyne: Unusual Formation of Acridone" has been published in Tetrahedron Lett.. You can find it at our publications page.

6.2012

• Congratulations to recent Stoltz group graduates! Keep up the hard work!

• The final projects for undergraduate organic chemistry course Ch 041c have been posted on YouTube. Enjoy cartoons, music videos and more on the Chemistry 041c page and learn while you watch!

3.2012

• Our recent review article, "A Comprehensive History of Arynes in Natural Product Total Synthesis" has been published in Chem. Rev. The paper may be found on our publications page.

1.2012

• Our recent publication, "Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams," has been discussed in a press release entitled "Caltech Chemists Devise Chemical Reaction that Holds Promise for New Drug Development". The paper may be found on our publications page.

• Our publication entitled "Benzuannulated Bicycles by Three-Component Aryne Reactions" was recently featured in a Highlight article in Angew. Chem. Int. Ed. See our publications page (#113) for links.

12.2011

• Our most recent publication entitled "Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams" has been published in Nature Chemistry. You may find it at our publications page.

11.2011

• Our most recent publication entitled " Palladium-catalyzed asymmetric alkylation in the synthesis of cyclopentanoid and cycloheptanoid core structures bearing all-carbon quaternary stereocenters" has been published in Tetrahedron. You may find it at our publications page.

• Our most recent publication entitled "Enantioselective Decarboxylative Alkylation Reactions: Catalyst Development, Substrate Scope, and Mechanistic Studies" has been published in Chemistry — A European Journal. You may find it at our publications page.

10.2011

• Our most recent publication entitled "Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems" has been published in Organic and Biomolecular Chemistry. You may find it at our publications page.

• Our publication on the enantioselective total synthesis of Liphagal was featured as the SYNFACT of the month for October! See our publications page (#116) for links.

8.2011

• Our publication on a palladium-catalyzed asymmetric Baeyer–Villiger reaction was highlighted in Organic Process Research and Development as an item of interest to Process Chemists and Engineers! See our See See our publications page (#115) for links

• Our recent publication on our approach to the Melodinus Alkaloids was one of the top 20 accessed publications in Organic Letters for the month of July!

• Our recent publication on our synthesis of the Integrastatin core was one of the top 10 accessed publications in Organic & Biomolecular Chemistry for the month of July! See See our publications page (#117) for links

7.2011

• Our paper on the synthesis of the Transtaganolides and Basiliolides was recently featured in synfacts! See our publications page (#112) for links.

• Our recent publication entitled "A Palladium-Catalyzed Vinylcyclopropane (3 + 2) Cycloaddition Approach to the Melodinus Alkaloids" has been published in Organic Letters and can be found on our publications page.

• Our recent full paper entitled "Total Syntheses of Cyanthiwigins B, F, and G" has been published in Chemistry – A European Journal and can be found on our publications page.

• Our recent publication entitled "Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters" was featured as the SYNFACT of the month! See our publications page (#114) for links.

6.2011

• Our latest publication, "A rapid and convergent synthesis of the integrastatin core", has been published in Organic & Biomolecular Chemistry and can be found on our publications page.

• Our latest publication, "The Catalytic Enantioselective Total Synthesis of (+)-Liphagal", has been published in Angewandte Chemie, International Edition and can be found on our publications page.

5.2011

• We've uploaded photos from our recent visit with the Raccoon Room: Teaching 4-year-olds about CO2! Check our "Photos" page by clicking here.

• Our publication entitled "Palladium-Catalyzed, asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones with PHOX ligands" has been published in Tetrahedron and can be found on our publications page.

4.2011

• Brian has been featured on the ABC Radio National's "The Science Show" in their installment "Making New Molecules". A link to the show can also be found on our chemistry links page.

• Our publication entitled "Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters" has been published in The Journal of the American Chemical Society and can be found on our publications page.

• Our most recent paper titled "Benzuannulated Bicycles by Three-Component Aryne Reactions" has been published in Angewandte Chemie, International Edition and can be found here.

3.2011

• Our most recent paper titled "A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D" has been published in Angewandte Chemie, International Edition and can be found here.

2.2011

• Our most recent paper titled "Ring-Contraction Strategy for the Practical, Scalable, Catalytic Asymmetric Synthesis of Versatile γ-Quaternary Acylcyclopentenes" has been published in Angewandte Chemie, International Edition and can be found here.

1.2011

• Our most recent paper titled "A Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran B" has been published in Organic Letters and can be found here.

• We are pleased to announce our collaboration with the Center for Stereoselective C-H Functionalization led by Prof. Huw Davies at Emory.

• We've updated our "Useful Chemistry Links" page with a link to a handy Chemistry Reference Resolver (also featured on our homepage), and a link to a useful OPR&D paper on polar solvent extraction. E-mail the webmaster if you have any suggestions!

• Congrats to Stoltz Group Alum, Uttam Tambar, on his first independent publication, titled "Catalytic Enantioselective [2,3]-Rearrangements of Amine N-Oxides."

12.2010

• Welcome to our new first-year graduate students: Rob, Doug, Christopher, Chung, Yiyang, and Corey.

• We have uploaded photos from a number of recent events to the website, including our Holiday Party, Brian's 40th, thesis defenses, and our pool party. These albums can be found here.

• Our most recent paper titled "Confirmation of the absolute configuration of (–)-aurantioclavine" has been published in Tetrahedron Letters and can be found here.

8.2010

• Our recent paper titled "Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides" has been published in Tetrahedron Letters and can be found here.

6.2010

• Our most recent paper titled "High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates" has been published in Synlett and can be found here.

• Our recent publication entitled "A palladium-catalysed enolate alkylation cascade for the formation of adjacent quaternary and tertiary stereocentres" was recently featured in C&E News and Synfacts. See our publications page (#100) for links.

5.2010

• Our newest publications are now online, entitled "A general enantioselective route to the chamigrene natural product family" and "Efforts toward rapid construction of the cortistatin A carbocyclic core via enyne-ene metathesis". These can be found here.

• Kathrin documented our move to Schlinger Laboratory and prepared a slide show for our move-in party - here are the slides!

• Have a look at our new Lab Tour page, featuring pictures from our new facility. More pictures of Schlinger Laboratory can also be found here.

• The group's review on Enantioselective Protonation has been featured in the Nature Chemistry first year anniversary highlights! Click here.

3.2010

• The group's latest collaborative publication titled "NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist" has been published in Organometallics and can be found here.

• The Stoltz Group is moving to our brand new home in the Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering. Pictures of the new facility can be found here. Photos documenting our move will be uploaded soon!

• The most recent publication from the group, entitled "Aryne Acyl-Alkylation in the General and Convergent Synthesis of Benzannulated Macrolactone Natural Products: An Enantioselective Synthesis of (–)-Curvularin", has been accepted and published in Organic Letters. Take a look here.

2.2010

• The group's latest publication titled "Regioselective Reactions of Highly Substituted Arynes" has been published in Organic Letters and can be found here.

• The group's latest publication titled "A palladium-catalysed enolate alkylation cascade for the formation of adjacent quaternary and tertiary stereocentres" has been published in Nature Chemistry and can be found here.

• The group's method for enantioselective alkylations of oxindoles has been featured in Synfacts, 2010, 65. A link to the article can be found here.


Click here for archived news.


Class Websites

Chemistry 242a - Organic Chemistry (Fall 2013)

Chemistry 41b - Organic Chemistry (Winter 2011)

Chemistry 41c - Organic Chemistry (Spring 2011)

Chemistry 41a - Organic Chemistry (Fall 2009)

Chemistry 5a - Advanced Techniques of Synthesis and Analysis (Spring 2003)

Chemistry 250 - Advances in Pharmaceutical Research (Spring 2011)

Chemistry 250 - Advances in Pharmaceutical Research (Spring 2003)


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