A general approach to the enantioselective α-oxidation of aldehydesvia synergistic catalysis

Scott P. Simonovich; Jeffrey F. Van Humbeck; David W. C. MacMillan

doi:10.1039/C1SC00556A

A general approach to the enantioselective α-oxidation of aldehydesvia synergistic catalysis

Scott P. Simonovich,^a Jeffrey F. Van Humbeck^a and David W. C. MacMillan*^a

* Corresponding authors

^a Merck Center for Catalysis at Princeton University, Princeton, USA
E-mail: dmacmill@princeton.edu
Fax: +1 609 2585922
Tel: +1 609 2582254

Abstract

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.

Supplementary files

Publication details

The article was received on 11 Aug 2011, accepted on 06 Sep 2011 and first published on 22 Sep 2011

Article type: Edge Article

DOI: 10.1039/C1SC00556A

Citation: Chem. Sci., 2012,3, 58-61

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A general approach to the enantioselective α-oxidation of aldehydesvia synergistic catalysis

S. P. Simonovich, J. F. Van Humbeck and D. W. C. MacMillan, Chem. Sci., 2012, 3, 58
DOI: 10.1039/C1SC00556A
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Chemical Science

A general approach to the enantioselective α-oxidation of aldehydesvia synergistic catalysis

Abstract

Supplementary files

Publication details

A general approach to the enantioselective α-oxidation of aldehydesvia synergistic catalysis

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