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

Jette, Carina I. and Geibel, Irina and Bachman, Shoshana and Hayashi, Masaki and Sakurai, Shunya and Shimizu, Hideki and Morgan, Jeremy B. and Stoltz, Brian M. (2019) Palladium-Catalyzed Construction of Quaternary Stereocenters by Enantioselective Arylation of γ-Lactams with Aryl Chlorides and Bromides. Angewandte Chemie International Edition, 58 (13). pp. 4297-4301. ISSN 1433-7851. http://resolver.caltech.edu/CaltechAUTHORS:20190124-110425627

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Abstract

Herein, we report the first Pd‐catalyzed enantioselective arylation of α‐substituted γ‐lactams. Two sets of conditions were developed for this transformation, allowing for the use of either aryl chlorides or bromides as electrophiles. Utilizing a highly electron‐rich, dialkylphosphine ligand, we have been able to construct α‐quaternary centers in good yields (up to 91% yield) and high enantioselectivities (up to 97% ee).


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/anie.201814475DOIArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. Accepted manuscript online: 24 January 2019; Manuscript accepted: 21 January 2019; Manuscript revised: 20 January 2019; Manuscript received: 20 December 2018. The NIH-NIGMS (R01GM080269) and Caltech are thanked for support of our research program. C. I. Jette thanks the National Science Foundation for a predoctoral fellowship. I. Geibel acknowledges the Deutsche Forschungsgemeinschaft (DFG) for a postdoctoral fellowship (GE 3082/1-1). H.S. thanks Shionogi & Co., Ltd. for a research grant and fellowship. J. B. Morgan acknowledges the University of North Carolina Wilmington for research reassignment and travel funds. Dr. Scott Virgil (Caltech) is thanked for instrumentation and SFC assistance.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
CaltechUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Deutsche Forschungsgemeinschaft (DFG)GE 3082/1-1
Shionogi & Co., Ltd.UNSPECIFIED
University of North CarolinaUNSPECIFIED
Subject Keywords:palladium; α-arylation; Nitrogen heterocycles; quaternary stereocenters; Asymmetric Catalysis
Record Number:CaltechAUTHORS:20190124-110425627
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20190124-110425627
Official Citation:C. I. Jette, I. Geibel, S. Bachman, M. Hayashi, S. Sakurai, H. Shimizu, J. B. Morgan, B. M. Stoltz, Angew. Chem. Int. Ed. 2019, 58, 4297; doi: 10.1002/anie.201814475
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:92451
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:24 Jan 2019 20:09
Last Modified:20 Mar 2019 16:16

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