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.

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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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