Enantioconvergent Cross−Couplings of Alkyl Electrophiles: The Catalytic Asymmetric Synthesis of Organosilanes
- Creators
-
Fu, Gregory C.
Abstract
Metal‐catalyzed enantioconvergent cross‐coupling reactions of alkyl electrophiles are emerging as a powerful tool in asymmetric synthesis. To date, high enantioselectivity has been limited to couplings of electrophiles that bear a directing group or a proximal p/π orbital. Herein, we demonstrate for the first time that enantioconvergent cross‐couplings can be achieved with electrophiles that lack such features; specifically, we establish that a chiral nickel catalyst can accomplish Negishi reactions of racemic α‐halosilanes with alkylzinc reagents with good enantioselectivity under simple and mild conditions, thereby providing access to enantioenriched organosilanes, an important class of target molecules.
Additional Information
© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. Manuscript received: December 13, 2018; Accepted manuscript online: January 16, 2019; Version of record online: February 5, 2019. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences; grant R01–GM062871 to G.C.F. and grant F32–GM116234 to G.M.S.) and the Dow Next Generation Educator Fund (grant to Caltech). We thank Dr. Jun Myun Ahn, Dr. Paul H. Oyala (Caltech EPR Facility), Dr. Mona Shahgholi (Caltech Mass Spectrometry Facility), Dr. Scott C. Virgil (Caltech Center for Catalysis and Chemical Synthesis), Dr. Haolin Yin, and Wanji Zhang for assistance and helpful discussions. The authors declare no conflict of interest.Attached Files
Accepted Version - Fu-2019-Angewandte_Chemie_International_Edition.pdf
Accepted Version - nihms-1008170.pdf
Supplemental Material - anie201814208-s1-supporting_information.pdf
Files
Additional details
- PMCID
- PMC6399024
- Eprint ID
- 92389
- DOI
- 10.1002/anie.201814208
- Resolver ID
- CaltechAUTHORS:20190122-084528318
- NIH
- R01 GM062871
- NIH Postdoctoral Fellowship
- F32 GM116234
- Dow Next Generation Educator Fund
- Created
-
2019-01-22Created from EPrint's datestamp field
- Updated
-
2021-11-16Created from EPrint's last_modified field