Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 21, Pages 5821-5824Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201702402
Keywords
alkylation; asymmetric synthesis; cross-coupling; nickel; zinc
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Funding
- National Institutes of Health (National Institute of General Medical Sciences) [R01-GM62871]
- Shanghai Institute of Organic Chemistry
- Japan Society for the Promotion of Science
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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.
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