CaltechAUTHORS
Published March 22, 2019 | Version Supplemental Material
Journal Article Open

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

Creators

  • 1. ROR icon California Institute of Technology
  • 2. ROR icon University of North Carolina Wilmington

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

Files

anie201814475-s1-carina_acie_lactam_arylation_full_si_final-v15-11719.pdf

Files (14.3 MB)

Additional details

Identifiers

Eprint ID
92451
Resolver ID
CaltechAUTHORS:20190124-110425627

Funding

NIH
R01GM080269
Caltech
NSF Predoctoral Fellowship
Deutsche Forschungsgemeinschaft (DFG)
GE 3082/1-1
Shionogi & Co., Ltd.
University of North Carolina

Dates

Created
2019-01-24
Created from EPrint's datestamp field
Updated
2021-11-16
Created from EPrint's last_modified field