Chemoenzymatic synthesis of alpha(1)- and alpha-acetoxylated cyclic ketones

Tanyeli C., Turkut E., Akhmedov M.

TETRAHEDRON-ASYMMETRY, vol.15, no.11, pp.1729-1733, 2004 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 15 Issue: 11
  • Publication Date: 2004
  • Doi Number: 10.1016/j.tetasy.2004.04.019
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1729-1733
  • Middle East Technical University Affiliated: Yes

Abstract

alpha,beta-Unsaturated and saturated cyclic ketones were selectively oxidized at the alpha'- and alpha-positions using Mn(OAc)(3) and Pb(OAc)(4), respectively, resulting in high chemical yields. The resultant racemic alpha'- and alpha-acetoxylated substrates were resolved into corresponding enantiomerically enriched alpha'- and alpha-hydroxylated and acetoxylated compounds with 96-98% ee via PLE hydrolysis. The absolute configurations of alpha'-acetoxy-alpha,beta-unsaturated cyclic ketones were determined by transforming them into the corresponding saturated alpha-acetoxy cyclic ketones of known absolute configuration. (C) 2004 Elsevier Ltd. All rights reserved.