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

Date

2004-06-07

Author

Tanyeli, Cihangir
Akhmedov, M

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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.

Subject Keywords

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

URI

https://hdl.handle.net/11511/41844

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2004.04.019

Collections

Department of Chemistry, Article

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Citation Formats

C. Tanyeli and M. Akhmedov, “Chemoenzymatic synthesis of alpha(1)- and alpha-acetoxylated cyclic ketones,” TETRAHEDRON-ASYMMETRY, pp. 1729–1733, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/41844.