Practical asymmetric Mukaiyama-Michael reaction of benzalacetone derivatives catalyzed by allo-threonine-derived oxazaborolidinone

Chirality. 2003 Jan;15(1):28-30. doi: 10.1002/chir.10161.

Abstract

In the presence of 2,6-diisopropylphenol and t-BuOMe (1 equiv. each), asymmetric Mukaiyama-Michael reaction of a variety of benzalacetone derivatives 2 with silyl ketene acetal 3 is efficiently catalyzed by O-(2-naphthoyl)-N-tosyl-(L)-allo-threonine-derived B-phenyloxazaborolidinone 1 (10 mol%) to give the corresponding adducts 5 in 60-90% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetone / analogs & derivatives*
  • Acetone / chemistry*
  • Benzene Derivatives / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Oxazoles / chemical synthesis
  • Oxazoles / chemistry*
  • Stereoisomerism
  • Threonine*

Substances

  • Benzene Derivatives
  • Oxazoles
  • Acetone
  • Threonine