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A general approach to the enantioselective ?-oxidation of aldehydes via synergistic catalysis.

ABSTRACT: A new enantioselective ?-oxidation of aldehydes has been accomplished using TEMPO and a synergistic combination of copper and organic catalysis. Expanding upon recently reported mechanistic studies, these mild catalytic conditions provide stable aldehyde products bearing a wide array of electronically and sterically diverse substructures. The utility of these oxidized products is highlighted by subsequent derivatization to a variety of common chiral synthons, without loss in enantiopurity.

SUBMITTER: Simonovich SP

PROVIDER: S-EPMC3269783 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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A general approach to the enantioselective α-oxidation of aldehydes via synergistic catalysis.

Simonovich Scott P SP Van Humbeck Jeffrey F JF Macmillan David W C DW

Chemical science 20120101 1

A new enantioselective α-oxidation of aldehydes has been accomplished using TEMPO and a synergistic combination of copper and organic catalysis. Expanding upon recently reported mechanistic studies, these mild catalytic conditions provide stable aldehyde products bearing a wide array of electronically and sterically diverse substructures. The utility of these oxidized products is highlighted by subsequent derivatization to a variety of common chiral synthons, without loss in enantiopurity. ...[more]

PMID: 22308217

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