The First Enantioselective Organocatalytic Mukaiyama-Michael Reaction: A Direct Method for the Synthesis of Enantioenriched -Butenol

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• 作者：Sean P. Brown ; Nicole C. Goodwin ; and David W. C. MacMillan
• 刊名：Journal of the American Chemical Society
• 出版年：2003
• 出版时间：February 5, 2003
• 年：2003
• 卷：125
• 期：5
• 页码：1192 - 1194
• 全文大小：106K
• 年卷期：v.125,no.5(February 5, 2003)
• ISSN：1520-5126

文摘

The first enantioselective organocatalytic Mukaiyama-Michael reaction using ,-unsaturated aldehydes has been accomplished. The use of iminium catalysis has provided a new strategy for the enantioselective addition of 2-silyloxy furans to unsaturated aldehydes to generate a variety of butenolide systems, an important chiral synthon found among many natural isolates. The (2S,5S)-5-benzyl-2-tert-butyl-imidazolidinone amine catalyst has been found to mediate the conjugate addition of a wide variety of substituted and unsubstituted silyloxy furans to unsaturated aldehydes. A diverse range of aldehyde substrates can be accommodated in this new organocatalytic transformation. Application of this new asymmetric technology to the enantioselective total synthesis of spiculisporic acid and the corresponding 5-epi-spiculisporic acid analogue is also discussed.