Chemoenzymatic synthesis of α ′- and α-acetoxylated cyclic ketones

Graphic α,β-Unsaturated and saturated cyclic ketones were selectively oxidized at the α ′- and α-positions using Mn(OAc) 3 and Pb(OAc) 4, respectively, resulting in high chemical yields. The resultant racemic α ′- and α-acetoxylated substrates were resolved into corresponding enantiomerically enrich...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2004-06, Vol.15 (11), p.1729-1733
Main Authors: Tanyeli, Cihangir, Turkut, Engin, Mecidoğlu Akhmedov, İdris
Format: Article
Language:English
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Summary:Graphic α,β-Unsaturated and saturated cyclic ketones were selectively oxidized at the α ′- and α-positions using Mn(OAc) 3 and Pb(OAc) 4, respectively, resulting in high chemical yields. The resultant racemic α ′- and α-acetoxylated substrates were resolved into corresponding enantiomerically enriched α ′- and α-hydroxylated and acetoxylated compounds with 96–98% ee via PLE hydrolysis. The absolute configurations of α ′-acetoxy-α,β-unsaturated cyclic ketones were determined by transforming them into the corresponding saturated α-acetoxy cyclic ketones of known absolute configuration.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2004.04.019