Stereoselective synthesis of optically active cyclitol precursors via a chemoenzymatic method

Oguzkaya F., Sahin E., Tanyeli C.

TETRAHEDRON-ASYMMETRY, vol.17, no.21, pp.3004-3009, 2006 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 21
  • Publication Date: 2006
  • Doi Number: 10.1016/j.tetasy.2006.11.002
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.3004-3009

Abstract

Racemic alpha'-acetoxy alpha,beta-unsaturated cyclohexanone has been converted to the corresponding enantiomerically enriched alpha'-hydroxylated and acetoxylated compounds with 97% ee via enzymatic resolution with PLE. OSO4-Catalyzed dihydroxylation of enantiomerically enriched alpha'-acetoxylated compound afforded a single diastereomer in 85% chemical yield. The absolute configuration of 2,3,6-triacetoxycylohexanone was determined by X-ray diffraction analysis. Subsequent Luche reduction allowed us to obtain corresponding syn-type cyclitol precursors in a highly stereoselective manner as expected. (c) 2006 Elsevier Ltd. All rights reserved.