Application of L-prolinamides as highly efficient organocatalysts for the asymmetric Michael addition of unmodified aldehydes to nitroalkenes

Naziroglu H. N., DURMAZ M., Bozkurt S., Demir A. S., SIRIT A.

TETRAHEDRON-ASYMMETRY, vol.23, no.2, pp.164-169, 2012 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 23 Issue: 2
  • Publication Date: 2012
  • Doi Number: 10.1016/j.tetasy.2012.01.008
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.164-169
  • Middle East Technical University Affiliated: Yes

Abstract

The asymmetric Michael addition of aldehydes to nitroolefins was investigated using a combination of L-prolinamide derivatives and various acidic additives. (S)-1,1'-Bi-2-naphthol was found to be the most effective co-catalyst and afforded the nitroaldehyde products with excellent yields (up to 95%), enantiomeric excesses (up to 99%) and diastereoselectivity ratios (up to 99:1). (C) 2012 Elsevier Ltd. All rights reserved.