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Org Lett. 2001 Feb 22;3(4):557-9. doi: 10.1021/ol006963k.

Enantioselective hydride abstraction in organic substrates: a novel use for chiral carbenium ions.

Organic letters

D Magdziak, L H Pettus, T R Pettus

Affiliations

  1. Department of Chemistry and Biochemistry, University of California at Santa Barbara, 93106, USA.

PMID: 11178824 DOI: 10.1021/ol006963k

Abstract

[reaction: see text] It is surprising that chiral cations have not been used to distinguish between prochiral hydrides when converse notions, such as asymmetric addition of a hyride to a prochiral functional group or use of a chiral anion to distinguish between a pair of prochiral protons, are methods employed everyday in enantioselective synthesis. To the best of our knowledge, this Letter describes the first example of an oxidative enantioselective hydride transfer process.

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