Reinvestigation of the synthetic and mechanistic aspects of Mn(III) acetate mediated oxidation of enones

Demir A., Reis O., Igdir A.

TETRAHEDRON, vol.60, no.15, pp.3427-3432, 2004 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 60 Issue: 15
  • Publication Date: 2004
  • Doi Number: 10.1016/j.tet.2004.02.039
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.3427-3432
  • Keywords: enones, oxidation, Mn(OAc)(3), alkenes, MANGANESE(III) ACETATE, ALPHA-ACETOXY, CLEAVAGE, 2-CYCLOHEXENONES, CYCLIZATIONS, ENANTIOMERS, KETONES
  • Middle East Technical University Affiliated: Yes

Abstract

Mn(OAc)(3) mediated alpha'-acetoxylation of alpha,beta-unsaturated enones is reinvestigated from a synthetic and mechanistic point of view and an improved procedure based on the use of acetic acid as a co-solvent is presented. Excellent results were obtained for a variety of structurally diverse and synthetically important enones under the optimized conditions. (C) 2004 Elsevier Ltd. All rights reserved.