The first enantioselective organocatalytic Mukaiyama-Michael reaction: a direct method for the synthesis of enantioenriched γ-butenolide architecture

…, NC Goodwin, DWC MacMillan

Index: Brown, Sean P.; Goodwin, Nicole C.; MacMillan, David W. C. Journal of the American Chemical Society, 2003 , vol. 125, # 5 p. 1192 - 1194

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Citation Number: 377

Abstract

The first enantioselective organocatalytic Mukaiyama-Michael reaction using α, β- 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 (2 S, 5 S)-5-benzyl-2-tert-butyl-imidazolidinone amine catalyst has ...