Stereoselective synthesis of optically active cyclitol precursors via a chemoenzymatic method
TETRAHEDRON-ASYMMETRY, vol.17, no.21, pp.3004-3009, 2006 (SCI-Expanded, Scopus)
- 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 (SCI-EXPANDED), Scopus
- Page Numbers: pp.3004-3009
- Middle East Technical University Affiliated: Yes
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.