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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
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F. Oguzkaya, E. Sahin, and C. Tanyeli, “Stereoselective synthesis of optically active cyclitol precursors via a chemoenzymatic method,”
TETRAHEDRON-ASYMMETRY
, pp. 3004–3009, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/48286.