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 | |||||||||
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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. | |||||||||
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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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