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Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides

DeLano, Travis J. and Dibrell, Sara E. and Lacker, Caitlin R. and Pancoast, Adam R. and Poremba, Kelsey E. and Cleary, Leah and Sigman, Matthew S. and Reisman, Sarah E. (2021) Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides. Chemical Science . ISSN 2041-6520. doi:10.1039/d1sc00822f. (In Press) https://resolver.caltech.edu/CaltechAUTHORS:20210113-152642442

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/d1sc00822fDOIArticle
http://www.rsc.org/suppdata/d1/sc/d1sc00822f/d1sc00822f1.pdfPublisherSupplementary Information
https://doi.org/10.26434/chemrxiv.13474638.v1DOIDiscussion Paper
ORCID:
AuthorORCID
DeLano, Travis J.0000-0002-2052-611X
Dibrell, Sara E.0000-0003-0332-1101
Lacker, Caitlin R.0000-0003-2531-2636
Pancoast, Adam R.0000-0002-1776-4950
Poremba, Kelsey E.0000-0002-7446-257X
Sigman, Matthew S.0000-0002-5746-8830
Reisman, Sarah E.0000-0001-8244-9300
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.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
NIHR35GM136271
NSF Graduate Research FellowshipDGE-1144469
Heritage Medical Research InstituteUNSPECIFIED
NIHR35GM118191
Royal Society of ChemistryUNSPECIFIED
DOI:10.1039/d1sc00822f
Record Number:CaltechAUTHORS:20210113-152642442
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210113-152642442
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:107462
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:13 Jan 2021 23:49
Last Modified:07 May 2021 17:16

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