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Published March 22, 2019 | Supplemental Material
Journal Article Open

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

Jette, Carina I. ORCID icon
Geibel, Irina
Bachman, Shoshana
Hayashi, Masaki
Sakurai, Shunya
Shimizu, Hideki
Morgan, Jeremy B.
Stoltz, Brian M. ORCID icon
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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).

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.

Attached Files

Supplemental Material - anie201814475-s1-carina_acie_lactam_arylation_full_si_final-v15-11719.pdf

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anie201814475-s1-carina_acie_lactam_arylation_full_si_final-v15-11719.pdf

Additional details

Identifiers Funding Dates
Created:
August 22, 2023
Modified:
October 20, 2023