New phosphine oxide aziridinyl phosphonates as chiral Lewis bases for the Abramov-type phosphonylation of aldehydes

DOĞAN Ö., Isci M., Aygun M.

TETRAHEDRON-ASYMMETRY, vol.24, pp.562-567, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 24
  • Publication Date: 2013
  • Doi Number: 10.1016/j.tetasy.2013.04.005
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.562-567
  • Middle East Technical University Affiliated: Yes

Abstract

A series of Lewis bases were screened for Abramov-type phosphine additions to aldehydes. A novel phosphine oxide aziridinyl phosphonate POAP-A was found to be better than the others in forming the product in 96% yield and with 42% ee. The absolute configuration of the newly synthesized POAP Lewis bases was determined by single-crystal X-ray analysis. (C) 2013 Elsevier Ltd. All rights reserved.