Pd-catalyzed asymmetric allylic amination of Morita-Baylis-Hillman adduct derivatives using chiral diaminophosphine oxides: DIAPHOXs

Org Lett. 2007 Mar 1;9(5):927-30. doi: 10.1021/ol0700207. Epub 2007 Feb 7.

Abstract

[reaction: see text] Asymmetric allylic amination of allylic carbonates prepared from racemic Morita-Baylis-Hillman adducts proceeded in the presence of Pd catalyst, chiral diaminophosphine oxide (DIAPHOX), and BSA, affording the corresponding chiral aza-Morita-Baylis-Hillman adduct derivatives in excellent yield with up to 99% ee. The cyclic reaction products could be converted into various synthetically useful compounds such as chiral cyclic beta-amino acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Molecular Structure
  • Oxides / chemistry*
  • Palladium / chemistry*
  • Phosphines / chemistry*
  • Stereoisomerism

Substances

  • Oxides
  • Phosphines
  • Palladium