Enantioselective enzymatic approach to (+)-and (-)-2-acetoxy/hydroxycyclopentanones

Easwar, Srinivasan ; Desai, Shrivallabh B. ; Argade, Narshinha P. ; Ganesh, Krishna N. (2002) Enantioselective enzymatic approach to (+)-and (-)-2-acetoxy/hydroxycyclopentanones Tetrahedron: Asymmetry, 13 (13). pp. 1367-1371. ISSN 0957-4166

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S09574...

Related URL: http://dx.doi.org/10.1016/S0957-4166(02)00366-X


A new practical enzymatic approach to (+)- and (-)-2-acetoxy/hydroxycyclopentanones with 96-98% ee has been described via enzymatic hydrolysis of the meso-diacetate 2, Swern oxidation of the thus formed (±)-hydroxy acetates 3 and 4, followed by re-enzymatic resolution. Enantiomerically pure (+)- and (-)-2-hydroxycyclopentanones are in equilibrium with enediol 9 and slowly undergo racemisation, a process which could be arrested by protecting the hydroxyl group as the acetate.

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ID Code:10842
Deposited On:09 Nov 2010 04:43
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