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

Sean P. Brown, Nicole C. Goodwin, David W.C. MacMillan

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395 Scopus citations

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 (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 discusse.

Original languageEnglish (US)
Pages (from-to)1192-1194
Number of pages3
JournalJournal of the American Chemical Society
Volume125
Issue number5
DOIs
StatePublished - Feb 5 2003

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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