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The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes

Brown, Sean P. and Brochu, Michael P. and Sinz, Christopher J. and MacMillan, David W. C. (2003) The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes. Journal of the American Chemical Society, 125 (36). pp. 10808-10809. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170419-130607059

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Abstract

The first direct enantioselective catalytic α-oxidation of carbonyls has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective oxyamination of aldehydes, to generate α-oxyaldehydes, important chiral synthons for natural product and medicinal agent synthesis. The use of l-proline as the asymmetric catalyst has been found to mediate the oxidation of a large variety of aldehyde substrates with nitrosobenzene serving as the electrophilic oxidant. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 2 mol % were generally employed in this study, successful oxidations conducted using catalyst loadings as low as 0.5 mol % are described.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja037096sDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja037096sPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja037096sPublisherSupporting Information
Additional Information:© 2003 American Chemical Society. Received 6 July 2003. Published online 19 August 2003. Published in print 1 September 2003. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Bristol-Myers Squibb, Johnson and Johnson, Lilly, and Merck Research Laboratories. D.W.C.M is grateful for support from the Sloan Foundation and Research Corporation. C.J.S. is grateful to the NIH for postdoctoral fellowship support (NIH-F32-CA-091635-01).
Funders:
Funding AgencyGrant Number
NIHR01 GM66142-01
Bristol-Myers SquibbUNSPECIFIED
Johnson and JohnsonUNSPECIFIED
LillyUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
Alfred P. Sloan FoundationUNSPECIFIED
Research CorporationUNSPECIFIED
NIH Postdoctoral FellowshipF32-CA-091635-01
Issue or Number:36
Record Number:CaltechAUTHORS:20170419-130607059
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170419-130607059
Official Citation:The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes Sean P. Brown, Michael P. Brochu, Christopher J. Sinz, and David W. C. MacMillan Journal of the American Chemical Society 2003 125 (36), 10808-10809 DOI: 10.1021/ja037096s
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76698
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:19 Apr 2017 21:54
Last Modified:03 Oct 2019 17:49

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