Self-assembly of an organocatalyst for the enantioselective synthesis of Michael adducts and alpha-aminoxy alcohols in a nonpolar medium

Demir A. S., BAŞÇEKEN S.

TETRAHEDRON-ASYMMETRY, vol.24, no.19, pp.1218-1224, 2013 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 24 Issue: 19
  • Publication Date: 2013
  • Doi Number: 10.1016/j.tetasy.2013.08.008
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1218-1224
  • Middle East Technical University Affiliated: No

Abstract

A proline-thiourea host-guest complex is described as a self-assembled organocatalyst for the enantioselective Michael addition of aldehydes to nitroolefins and for the asymmetric alpha-aminoxylation of both aldehydes and ketones. The Michael adducts were obtained in good yields of up to 80%, high diastereo-selectivities of up to 5:95, and high enantiomeric excesses of up to 98%. The optically active aminoxy alcohols were synthesized in 60-85% yields with 94-99% enantiomeric excesses after reduction of the alpha-oxidation products using NaBH4. (C) 2013 Elsevier Ltd. All rights reserved.