The First Enantioselective Organocatalytic Mukaiyama−Michael Reaction: A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture
2003; American Chemical Society; Volume: 125; Issue: 5 Linguagem: Inglês
10.1021/ja029095q
ISSN1943-2984
AutoresSean P. Brown, Nicole C. Goodwin, David W. C. MacMillan,
Tópico(s)Traditional and Medicinal Uses of Annonaceae
ResumoThe 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 (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.
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