Organocatalytic asymmetric transformations of modified Morita-Baylis-Hillman adducts

Chem Soc Rev. 2012 Jun 7;41(11):4101-12. doi: 10.1039/c2cs35017c. Epub 2012 Mar 28.

Abstract

Chiral Lewis basic tertiary amines or phosphines can enable properly modified Morita-Baylis-Hillman (MBH) adducts to undergo asymmetric allylic substitutions with a wide range of nucleophiles. In addition, assisted by a Brønsted base, chiral Lewis bases can also catalytically convert modified MBH adducts into allylic ylides, which can be engaged in a variety of asymmetric annulation reactions. This tutorial review will focus on such chiral Lewis base-catalysed asymmetric transformations of MBH adducts, especially those developed over the past five years, allowing for the rapid construction of densely functionalised chiral molecules with high levels of regio- and stereoselectivities.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Alkylation
  • Amines / chemistry
  • Catalysis
  • Cyclization
  • Lewis Bases / chemistry*
  • Phosphines / chemistry
  • Stereoisomerism

Substances

  • Amines
  • Lewis Bases
  • Phosphines