Published June 14, 2021
| Supplemental Material + Submitted + Published
Journal Article
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Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides
Abstract
An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities. The reaction is tolerant of a variety of functional groups, and the resulting products can be converted to pharmaceutically-relevant chiral building blocks. A multivariate linear regression model was developed to quantitatively relate the influence of the α-chloroester substrate and ligand on enantioselectivity.
Additional Information
© 2021 The Author(s). Published by the Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. All publication charges for this article have been paid for by the Royal Society of Chemistry. Submitted 09 Feb 2021; Accepted 24 Apr 2021; First published 26 Apr 2021. Dr Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis are gratefully acknowledged for access to analytical equipment. We thank Yoshihiro Ogura for early studies and Raymond Turro for the preparation of L1. M. S. S. thanks the NIH (R35GM136271) for support. Fellowship support was provided by the NSF (T. J. D., S. E. D., C. R. L., K. E. P., Grant No. DGE-1144469). S. E. R. is a Heritage Medical Research Institute Investigator, and acknowledges financial support from the NIH (R35GM118191). Author contributions: S. E. R., L. C., K. E. P., and T. J. D. conceptualized the project. T. J. D., S. E. D., C. R. L., K. E. P., and L. C. carried out the experimental investigations. A. R. P. carried out the MLR modeling studies. M. S. S. supervised the modeling studies. S. E. R. supervised the experimental investigations. T. J. D., S. E. D., C. R. L., K. E. P., A. R. P., M. S. S. and S. E. R. wrote and edited the manuscript. There are no conflicts to declare.Attached Files
Published - d1sc00822f.pdf
Submitted - Nickel-Catalyzed_Asymmetric_Reductive_Cross-Coupling_of_a-Chloroesters_with__Hetero_Aryl_Iodides_v1.pdf
Supplemental Material - d1sc00822f1.pdf
Files
d1sc00822f.pdf
Additional details
- PMCID
- PMC8188512
- Eprint ID
- 107462
- Resolver ID
- CaltechAUTHORS:20210113-152642442
- R35GM136271
- NIH
- DGE-1144469
- NSF Graduate Research Fellowship
- Heritage Medical Research Institute
- R35GM118191
- NIH
- Royal Society of Chemistry
- Created
-
2021-01-13Created from EPrint's datestamp field
- Updated
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2021-06-25Created from EPrint's last_modified field
- Caltech groups
- Heritage Medical Research Institute