Chiral phosphine oxide aziridinyl phosphonate as a Lewis base catalyst for enantioselective allylsilane addition to aldehydes

DOĞAN Ö., Bulut A., Tecimer M. A.

TETRAHEDRON-ASYMMETRY, vol.26, no.17, pp.966-969, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 26 Issue: 17
  • Publication Date: 2015
  • Doi Number: 10.1016/j.tetasy.2015.07.002
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.966-969
  • Middle East Technical University Affiliated: Yes

Abstract

A series of chiral Lewis bases, phosphine oxide ferrocenyl aziridinyl methanol 1-4, phosphinyl aziridinyl phosphonates 5 and 6, and phosphine oxide aziridinyl phosphonates 7 and 8 were screened for allylsilane additions to aldehydes. Among the Lewis bases, 8 was found to catalyze the reaction by forming the product in up to 94% yield and with 77% ee. (C) 2015 Elsevier Ltd. All rights reserved.