Stoltz, Brian

Article from CaltechAUTHORS

• Moghadam, Farbod A. and Barbor, Jay P., et el. (2024) Formation of All-Carbon Quaternary Centers via Enantioselective Pd-Catalyzed α-Vinylation of γ-Lactams; Organic Letters; Vol. 26; No. 36; 7551–7554; 10.1021/acs.orglett.4c02551
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• Gross, Benjamin M. and Stoltz, Brian M. (2024) Convenient access to a strained bicyclic enone: A concise and improved formal synthesis of ineleganolide; Tetrahedron Letters; Vol. 140; 155011; 10.1016/j.tetlet.2024.155011
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• Xu, Yinchao and Stanko, Allison M., et el. (2024) Low Part-Per-Trillion, Humidity Resistant Detection of Nitric Oxide Using Microtoroid Optical Resonators; ACS Applied Materials & Interfaces; Vol. 16; No. 4; 5120-5128; 10.1021/acsami.3c16012
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• Stoltz, Brian M. (2023) Editorial for special issue in honor of Professor John Wood; Tetrahedron; Vol. 148; 133700; 10.1016/j.tet.2023.133700
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• Cusumano, Alexander and Zhang, Tianyi, et el. (2023) Origins of Enhanced Enantioselectivity in the Pd-Catalyzed Decarboxylative Allylic Alkylation of N-Benzoyl Lactams; Catalysts; Vol. 13; No. 9; 1258; PMCID PMC10662798; 10.3390/catal13091258
• Kim, Alexia N. and Ngamnithiporn, Aurapat, et el. (2023) Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020); Chemical Reviews; Vol. 123; No. 15; 9447-9496; PMCID PMC10416225; 10.1021/acs.chemrev.3c00054
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• Greßies, Steffen and Süße, Lars, et el. (2023) Tandem Dearomatization/Enantioselective Allylic Alkylation of Pyridines; Journal of the American Chemical Society; Vol. 145; No. 22; 11907-11913; PMCID PMC10251512; 10.1021/jacs.3c02470
• Flesch, Kaylin N. and Cusumano, Alexander Q., et el. (2023) Divergent Catalysis: Catalytic Asymmetric [4+2] Cycloaddition of Palladium Enolates; Journal of the American Chemical Society; Vol. 145; No. 20; 11301-11310; PMCID PMC10388310; 10.1021/jacs.3c02104
• Hafeman, Nicholas J. and Loskot, Steven A., et el. (2023) Total synthesis of (−)-scabrolide A and (−)-yonarolide; Chemical Science; Vol. 14; No. 18; 4745-4758; PMCID PMC10173254; 10.1039/d3sc00651d
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• Rand, Alexander W. and Gonzalez, Kevin J., et el. (2023) Total Synthesis of Strempeliopidine and Non-Natural Stereoisomers through a Convergent Petasis Borono-Mannich Reaction; Journal of the American Chemical Society; Vol. 145; No. 13; 7278-7287; PMCID PMC10281614; 10.1021/jacs.2c13146
• Gonzalez, Kevin J. and Rand, Alexander W., et el. (2023) Development of a Non‐Directed Petasis‐Type Reaction by an Aromaticity‐Disrupting Strategy; Angewandte Chemie International Edition; Vol. 62; No. 14; e202218921; PMCID PMC10033435
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• Hafeman, Nicholas J. and Chan, Melinda, et el. (2022) Asymmetric Total Synthesis of Havellockate; Journal of the American Chemical Society; Vol. 144; No. 44; 20232-20236; PMCID PMC9997676; 10.1021/jacs.2c09583
• Zhang, Tianyi and Cusumano, Alexander Q., et el. (2022) Investigations of an Unexpected [2+2] Photocycloaddition in the Synthesis of (−)-Scabrolide A from Quantum Mechanics Calculations; Journal of Organic Chemistry; Vol. 87; No. 21; 14115-14124; 10.1021/acs.joc.2c01693
• Goldstein, Elizabeth L. and Takada, Hirokazu, et el. (2022) Synthesis of enantioenriched 2,2-disubstituted pyrrolidines via sequential asymmetric allylic alkylation and ring contraction; Tetrahedron; Vol. 123; Art. No. 132940; PMCID PMC10038171; 10.1016/j.tet.2022.132940
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• Kim, Alexia N. and Ngamnithiporn, Aurapat, et el. (2022) Iridium-catalyzed asymmetric trans-selective hydrogenation of 1,3-disubstituted isoquinolines; Chemical Science; Vol. 13; No. 11; 3227-3232; PMCID PMC8926345; 10.1039/d1sc06729j
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• Kim, Kelly E. and Kim, Alexia N., et el. (2021) Late-Stage Diversification: A Motivating Force in Organic Synthesis; Journal of the American Chemical Society; Vol. 143; No. 41; 16890-16901; PMCID PMC9285880; 10.1021/jacs.1c08920
• Sercel, Zachary P. and Sun, Alexander W., et el. (2021) Synthesis of Enantioenriched gem-Disubstituted 4-Imidazolidinones by Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation; Organic Letters; Vol. 23; No. 16; 6348-6351; PMCID PMC8534816; 10.1021/acs.orglett.1c02134
• Lohrey, Trevor D. and Cusumano, Alexander Q., et el. (2021) Identifying the Imperative Role of Metal–Olefin Interactions in Catalytic C–O Reductive Elimination from Nickel(II); ACS Catalysis; Vol. 11; No. 16; 10208-10222; PMCID PMC8849544; 10.1021/acscatal.1c02790
• Reimann, Christopher E. and Ngamnithiporn, Aurapat, et el. (2021) The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16′-epi-Leucophyllidine; Angewandte Chemie International Edition; Vol. 60; No. 33; 17957-17962; PMCID PMC8338904; 10.1002/anie.202106184
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• Han, Seo-Jung and Cavitt, Marchello A., et el. (2021) A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement; Organic Letters; Vol. 23; No. 9; 3300-3303; PMCID PMC8846577; 10.1021/acs.orglett.1c00763
• Süsse, Lars and Stoltz, Brian M. (2021) Enantioselective Formation of Quaternary Centers by Allylic Alkylation with First-Row Transition-Metal Catalysts; Chemical Reviews; Vol. 121; No. 7; 4084-4099; PMCID PMC8846597; 10.1021/acs.chemrev.0c01115
• Zhang, Gang and Li, Shan, et el. (2021) A covalent p97/VCP ATPase inhibitor can overcome resistance to CB-5083 and NMS-873 in colorectal cancer cells; European Journal of Medicinal Chemistry; Vol. 213; Art. No. 113148; PMCID PMC7954469; 10.1016/j.ejmech.2020.113148
• Sardini, Stephen R. and Stoltz, Brian M. (2021) Discussion Addendum for: Preparation of (S)-tert-ButylPyOx and Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids; Organic Syntheses; Vol. 98; 117-130; PMCID PMC9558615; 10.15227/orgsyn.098.0117
• Fulton, Tyler J. and Cusumano, Alexander Q., et el. (2020) Global Diastereoconvergence in the Ireland–Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids; Journal of the American Chemical Society; Vol. 142; No. 52; 21938-21947; PMCID PMC8552564; 10.1021/jacs.0c11480
• Kim, Kelly E. and Sakazaki, Yuka, et el. (2020) Synthesis of non-natural cyanthiwigin–gagunin hybrids through late-stage diversification of the cyanthiwigin natural product core; Tetrahedron; Vol. 76; No. 51; Art. No. 130755; 10.1016/j.tet.2019.130755
• Kim, Alexia N. and Stoltz, Brian M. (2020) Recent Advances in Homogeneous Catalysts for the Asymmetric Hydrogenation of Heteroarenes; ACS Catalysis; Vol. 10; No. 23; 13834-13851; PMCID PMC8460131; 10.1021/acscatal.0c03958
• Cusumano, Alexander Q. and Goddard, William A., III, et el. (2020) Transition Metal Catalyzed [π2s + π2s + σ2s + σ2s] Pericyclic Reaction: Woodward–Hoffmann Rules, Aromaticity, and Electron Flow; Journal of the American Chemical Society; Vol. 142; No. 45; 19033-19039; PMCID PMC8549492; 10.1021/jacs.0c09575
• Ngamnithiporn, Aurapat and Iwayama, Toshihiko, et el. (2020) Enantioselective synthesis of highly oxygenated acyclic quaternary center-containing building blocks via palladium-catalyzed decarboxylative allylic alkylation of cyclic siloxyketones; Chemical Science; Vol. 11; No. 40; 11068-11071; PMCID PMC8162308; 10.1039/d0sc04383d
• Fulton, Tyler J. and Chen, Anthony Y., et el. (2020) Enantioselective Total Synthesis of (–)-Myrifabral A and B; Chemical Science; Vol. 11; No. 39; 10802-10806; PMCID PMC8162428; 10.1039/d0sc01141j
• Kenseth, Christopher M. and Hafeman, Nicholas J., et el. (2020) 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; Environmental Science and Technology; Vol. 54; No. 20; 12829-12839; 10.1021/acs.est.0c01566
• Wolf, William J. and Li, Jiaming, et el. (2020) Efficient Synthesis of Geminal-Dialkyl Dienes for Olefin Metathesis Polymerization; Macromolecules; Vol. 53; No. 18; 7803-7809; PMCID PMC8297823; 10.1021/acs.macromol.0c01606
• Cusumano, Alexander Q. and Stoltz, Brian M., et el. (2020) 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; Journal of the American Chemical Society; Vol. 142; No. 32; 13917-13933; PMCID PMC7802888; 10.1021/jacs.0c06243
• Inanaga, Kazato and Wollenburg, Marco, et el. (2020) Catalytic enantioselective synthesis of carbocyclic and heterocyclic spiranes via a decarboxylative aldol cyclization; Chemical Science; Vol. 11; No. 28; 7390-7395; PMCID PMC7574022; 10.1039/d0sc02366c
• Duquette, Douglas C. and Cusumano, Alexander Q., et el. (2020) Probing Trends in Enantioinduction via Substrate Design: Palladium-Catalyzed Decarboxylative Allylic Alkylation of α-Enaminones; Organic Letters; Vol. 22; No. 13; 4966-4969; PMCID PMC7608880; 10.1021/acs.orglett.0c01441
• Lavernhe, Rémi and Alexy, Eric J., et el. (2020) Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones; Organic Letters; Vol. 22; No. 11; 4272-4275; PMCID PMC7608871; 10.1021/acs.orglett.0c01303
• Baek, Doohyun and Ryu, Huijeong, et el. (2020) Catalytic enantioselective synthesis of tetrasubstituted chromanones via palladium-catalyzed asymmetric conjugate arylation using chiral pyridine-dihydroisoquinoline ligands; Chemical Science; Vol. 11; No. 18; 4602-4607; PMCID PMC7574023; 10.1039/d0sc00412j
• Hafeman, Nicholas J. and Loskot, Steven A., et el. (2020) The Total Synthesis of (–)-Scabrolide A; Journal of the American Chemical Society; Vol. 142; No. 19; 8585-8590; 10.1021/jacs.0c02513
• Kim, Alexia N. and Ngamnithiporn, Aurapat, et el. (2020) Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of 1,3-Disubstituted Isoquinolines; ACS Catalysis; Vol. 10; No. 5; 3241-3248; PMCID PMC8152574; 10.1021/acscatal.0c00211
• Jette, Carina I. and Tong, Z. Jaron, et el. (2020) Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal; Angewandte Chemie International Edition; Vol. 59; No. 5; 2033-2038; PMCID PMC7051182; 10.1002/anie.201912618
• Lavernhe, Rémi and Alexy, Eric J., et el. (2020) Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Protected Benzoin-Derived Enol Carbonates; Advanced Synthesis and Catalysis; Vol. 362; No. 2; 344-347; PMCID PMC7942817; 10.1002/adsc.201901281
• Park, Dongseong and Jette, Carina I., et el. (2020) Enantioselective Alkynylation of Trifluoromethyl Ketones Catalyzed by Cation-Binding Salen Nickel Complexes; Angewandte Chemie International Edition; Vol. 59; No. 2; 775-779; 10.1002/anie.201913057
• Li, Jiaming and Stoltz, Brian M., et el. (2019) Enantioselective Synthesis of 15-Deoxy-Δ¹²,¹⁴-Prostaglandin J₂; Organic Letters; Vol. 21; No. 24; 10139-10142; 10.1021/acs.orglett.9b04198
• Wright, Austin C. and Stoltz, Brian M. (2019) Enantioselective construction of the tricyclic core of curcusones A–D via a cross-electrophile coupling approach; Chemical Science; Vol. 10; No. 45; 10562-10565; PMCID PMC6988747; 10.1039/c9sc04127c
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• Velasco-Rubio, Álvaro and Alexy, Eric J., et el. (2019) Stereospecific Overman Rearrangement of Substituted Cyclic Vinyl Bromides: Access to Fully Substituted α-Amino Ketones; Organic Letters; Vol. 21; No. 22; 8962-8965; 10.1021/acs.orglett.9b03347
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• Alexy, Eric J. and Fulton, Tyler J., et el. (2019) Palladium-catalyzed enantioselective decarboxylative allylic alkylation of fully substituted N-acyl indole-derived enol carbonates; Chemical Science; Vol. 10; No. 23; 5996-6000; PMCID PMC6566452; 10.1039/c9sc01726g
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• Wright, Austin C. and Stoltz, Brian M. (2019) Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2-(2-acetylphenyl)acetate; Organic Syntheses; Vol. 96; 80-97
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• Jette, Carina I. and Geibel, Irina, et el. (2019) Palladium-Catalyzed Construction of Quaternary Stereocenters by Enantioselective Arylation of γ-Lactams with Aryl Chlorides and Bromides; Angewandte Chemie International Edition; Vol. 58; No. 13; 4297-4301; 10.1002/anie.201814475
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• Li, Jiaming and Ahmed, Tonia S., et el. (2019) Concise Syntheses of Δ^(12)-Prostaglandin J Natural Products via Stereoretentive Metathesis; Journal of the American Chemical Society; Vol. 141; No. 1; 154-158; 10.1021/jacs.8b12816
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• Lu, Yanhui and Goldstein, Elizabeth L., et el. (2018) Palladium-Catalyzed Enantioselective C_(sp)^3–C_(sp)^3 Cross-Coupling for the Synthesis of (Poly)fluorinated Chiral Building Blocks; Organic Letters; Vol. 20; No. 18; 5657-5660; PMCID PMC6192028; 10.1021/acs.orglett.8b02369
• Wang, Xin and Zhu, Ming-Hui, et el. (2018) General and Practical Potassium Methoxide/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Arylhalides; Journal of the American Chemical Society; Vol. 140; No. 35; 10970-10974; 10.1021/jacs.8b07597
• Alexy, Eric J. and Zhang, Haiming, et el. (2018) Catalytic Enantioselective Synthesis of Acyclic Quaternary Centers: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Acyclic Enol Carbonates; Journal of the American Chemical Society; Vol. 140; No. 32; 10109-10112; PMCID PMC6103296; 10.1021/jacs.8b05560
• Kenseth, Christopher M. and Huang, Yuanlong, et el. (2018) Synergistic O₃ + OH oxidation pathway to extremely low-volatility dimers revealed in β-pinene secondary organic aerosol; Proceedings of the National Academy of Sciences of the United States of America; Vol. 115; No. 33; 8301-8306; PMCID PMC6099901; 10.1073/pnas.1804671115
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• Hartrampf, Nina and Winter, Nils, et el. (2018) Total Synthesis of the Norhasubanan Alkaloid Stephadiamine; Journal of the American Chemical Society; Vol. 140; No. 28; 8675-8680; PMCID PMC6130314; 10.1021/jacs.8b01918
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• Zhang, Haiming and Ferreira, Eric M., et el. (2004) Direct Oxidative Heck Cyclizations: Intramolecular Fujiwara-Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans; Angewandte Chemie International Edition; Vol. 43; No. 45; 6144-6148; 10.1002/anie.200461294
• Garg, Neil K. and Caspi, Daniel D., et el. (2004) The Total Synthesis of (+)-Dragmacidin F; Journal of the American Chemical Society; Vol. 126; No. 31; 9552-9553; 10.1021/ja046695b
• Nielsen, Robert J. and Keith, Jason M., et el. (2004) A Computational Model Relating Structure and Reactivity in Enantioselective Oxidations of Secondary Alcohols by (−)-Sparteine−Pd^(II) Complexes; Journal of the American Chemical Society; Vol. 126; No. 25; 7967-7974; 10.1021/ja031911m
• Trend, Raissa M. and Stoltz, Brian M. (2004) An Experimentally Derived Model for Stereoselectivity in the Aerobic Oxidative Kinetic Resolution of Secondary Alcohols by (Sparteine)PdCl_2; Journal of the American Chemical Society; Vol. 126; No. 14; 4482-4483; 10.1021/ja039551q
• Su, Julius T. and Sarpong, Richmond, et el. (2004) Substituent Effects and Nearly Degenerate Transition States: Rational Design of Substrates for the Tandem Wolff−Cope Reaction; Journal of the American Chemical Society; Vol. 126; No. 1; 24-25; 10.1021/ja037716p
• Bagdanoff, Jeffrey T. and Stoltz, Brian M. (2004) Palladium-Catalyzed Oxidative Kinetic Resolution with Ambient Air as the Stoichiometric Oxidation Gas; Angewandte Chemie International Edition; Vol. 43; No. 3; 353-357; 10.1002/anie.200352444
• Ashley, Eric R. and Cruz, Ernest G., et el. (2003) The Total Synthesis of (−)-Lemonomycin; Journal of the American Chemical Society; Vol. 125; No. 49; 15000-15001; 10.1021/ja039223q
• Sarpong, Richmond and Su, Julius T., et el. (2003) The Development of a Facile Tandem Wolff/Cope Rearrangement for the Synthesis of Fused Carbocyclic Skeletons; Journal of the American Chemical Society; Vol. 125; No. 45; 13624-13625; 10.1021/ja037587c
• Ferreira, Eric M. and Stoltz, Brian M. (2003) Catalytic C−H Bond Functionalization with Palladium(II): Aerobic Oxidative Annulations of Indoles; Journal of the American Chemical Society; Vol. 125; No. 32; 9578-9579; 10.1021/ja035054y
• Trend, Raissa M. and Ramtohul, Yeeman K., et el. (2003) Palladium-Catalyzed Oxidative Wacker Cyclizations in Nonpolar Organic Solvents with Molecular Oxygen: A Stepping Stone to Asymmetric Aerobic Cyclizations; Angewandte Chemie International Edition; Vol. 42; No. 25; 2892-2895; 10.1002/anie.200351196
• Julian, Ryan R. and May, Jeremy A., et el. (2003) Gas-Phase Synthesis of Charged Copper and Silver Fischer Carbenes from Diazomalonates: Mechanistic and Conformational Considerations in Metal-Mediated Wolff Rearrangements; Journal of the American Chemical Society; Vol. 125; No. 15; 4478-4486; 10.1021/ja028337j
• Bagdanoff, Jeffrey T. and Ferreira, Eric M., et el. (2003) Palladium-Catalyzed Enantioselective Oxidation of Alcohols: A Dramatic Rate Acceleration by Cs_2CO_3/t-BuOH; Organic Letters; Vol. 5; No. 6; 835-837; 10.1021/ol027463p
• Julian, Ryan R. and May, Jeremy A., et el. (2003) Molecular Mousetraps: Gas-Phase Studies of the Covalent Coupling of Noncovalent Complexes Initiated by Reactive Carbenes Formed by Controlled Activation of Diazo Precursors; Angewandte Chemie International Edition; Vol. 42; No. 9; 1012-1015; 10.1002/anie.200390258
• Garg, Neil K. and Sarpong, Richmond, et el. (2002) The First Total Synthesis of Dragmacidin D; Journal of the American Chemical Society; Vol. 124; No. 44; 13179-13184; 10.1021/ja027822b
• May, Jeremy A. and Stoltz, Brian M. (2002) Non-Carbonyl-Stabilized Metallocarbenoids in Synthesis: The Development of a Tandem Rhodium-Catalyzed Bamford−Stevens/Thermal Aliphatic Claisen Rearrangement Sequence; Journal of the American Chemical Society; Vol. 124; No. 42; 12426-12427; 10.1021/ja028020j
• Spessard, Sarah J. and Stoltz, Brian M. (2002) Progress toward the Synthesis of Garsubellin A and Related Phloroglucins: The Direct Diastereoselective Synthesis of the Bicyclo[3.3.1]nonane Core; Organic Letters; Vol. 4; No. 11; 1943-1946; 10.1021/ol025968+
• Ferreira, Eric M. and Stoltz, Brian M. (2001) The Palladium-Catalyzed Oxidative Kinetic Resolution of Secondary Alcohols with Molecular Oxygen; Journal of the American Chemical Society; Vol. 123; No. 31; 7725-7726; 10.1021/ja015791z
• Fuerst, Douglas E. and Stoltz, Brian M., et el. (2000) Synthesis of C(3) Benzofuran-Derived Bisaryl Quaternary Centers: Approaches to Diazonamide A; Organic Letters; Vol. 2; No. 22; 3521-3523; 10.1021/ol006578v
• Ge, Min and Stoltz, Brian M., et el. (2000) Mechanistic Insights into the Factors Determining Exo−EndoSelectivity in the Lewis Acid-Catalyzed Diels−Alder Reaction of 1,3-Dienes with 2-Cycloalkenones; Organic Letters; Vol. 2; No. 13; 1927-1929; 10.1021/ol0060026