Stereoselective synthesis of optically active cyclitol precursors via a chemoenzymatic method

Date

2006-11-17

Author

Oguzkaya, Funda
Sahin, Ertan
Tanyeli, Cihangir

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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.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/48286

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2006.11.002

Collections

Department of Chemistry, Article

Citation Formats

F. Oguzkaya, E. Sahin, and C. Tanyeli, “Stereoselective synthesis of optically active cyclitol precursors via a chemoenzymatic method,” TETRAHEDRON-ASYMMETRY, vol. 17, no. 21, pp. 3004–3009, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/48286.