The Direct and Enantioselective Organocatalytic -Oxidation of Aldehydes

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• 作者：Sean P. Brown ; Michael P. Brochu ; Christopher J. Sinz ; and David W. C. MacMillan
• 刊名：Journal of the American Chemical Society
• 出版年：2003
• 出版时间：September 10, 2003
• 年：2003
• 卷：125
• 期：36
• 页码：10808 - 10809
• 全文大小：57K
• 年卷期：v.125,no.36(September 10, 2003)
• ISSN：1520-5126

文摘

The first direct enantioselective catalytic -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 -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.