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Control of Vicinal Stereocenters through Nickel-Catalyzed Alkyl-Alkyl Cross-Coupling

Mu, Xin and Shibata, Yu and Makida, Yusuke and Fu, Gregory C. (2017) Control of Vicinal Stereocenters through Nickel-Catalyzed Alkyl-Alkyl Cross-Coupling. Angewandte Chemie International Edition, 56 (21). pp. 5821-5824. ISSN 1433-7851. PMCID PMC5595219. doi:10.1002/anie.201702402. https://resolver.caltech.edu/CaltechAUTHORS:20170419-135029412

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Abstract

Vicinal stereocenters are found in many natural and unnatural compounds. Although metal-catalyzed cross-coupling reactions of unactivated alkyl electrophiles are emerging as a powerful tool in organic synthesis, there have been virtually no reports of processes that generate, much less control, vicinal stereocenters. In this investigation, we establish that a chiral nickel catalyst can mediate doubly stereoconvergent alkyl–alkyl cross-coupling, specifically, reactions of a racemic pyrrolidine-derived nucleophile with cyclic alkyl halides (as mixtures of stereoisomers) to produce vicinal stereocenters with very good stereoselectivity.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/anie.201702402DOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5595219PubMed CentralArticle
ORCID:
AuthorORCID
Fu, Gregory C.0000-0002-0927-680X
Alternate Title:Control of Vicinal Stereocenters via Nickel-Catalyzed Alkyl–Alkyl Cross-Coupling
Additional Information:© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Manuscript received: March 6, 2017; Final Article published: April 19, 2017. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences: R01-GM62871), the Shanghai Institute of Organic Chemistry (fellowship to X.M.), and the Japan Society for the Promotion of Science (fellowship to Y.M.). We thank Jun Myun Ahn (x-ray crystallography), Lawrence M. Henling (Caltech X-Ray Crystallography Facility), Dr. Nathan Schley (x-ray crystallography), Samantha E. Shockley (Stoltz lab), Dr. Scott C. Virgil (Caltech Center for Catalysis and Chemical Synthesis), Dr. David G. VanderVelde (Caltech NMR facility), and Dr. Haolin Yin for assistance. The authors declare no conflict of interest.
Funders:
Funding AgencyGrant Number
NIHR01-GM62871
Shanghai Institute of Organic Chemistry (SIOC)UNSPECIFIED
Japan Society for the Promotion of Science (JSPS)UNSPECIFIED
Subject Keywords:alkylation; asymmetric synthesis; cross-coupling; nickel; zinc
Issue or Number:21
PubMed Central ID:PMC5595219
DOI:10.1002/anie.201702402
Record Number:CaltechAUTHORS:20170419-135029412
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170419-135029412
Official Citation:X. Mu, Y. Shibata, Y. Makida, G. C. Fu, Angew. Chem. Int. Ed. 2017, 56, 5821
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76704
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:19 Apr 2017 21:45
Last Modified:15 Nov 2021 17:02

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