Desymmetrization of meso-cyclopenten- cis-1,4-diol to 4-( R)-hydroxycyclopent-2-en-1-( S)-acetate by irreversible transesterification using Chirazyme

The parameter optimization study for the desymmetrization of meso-cyclopenten-1,4-diol 1 through irreversible transesterification using an immobilized lipase from Mucor meihei, i.e., Lipozyme ®/Chirazyme ® is presented. The enzyme was studied for the transesterification of 1 in various organic solve...

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Published in:Tetrahedron: asymmetry 1999-03, Vol.10 (5), p.891-899
Main Authors: Ghorpade, Sandeep R, Kharul, Rajendra K, Joshi, Rohini R, Kalkote, Uttam R, Ravindranathan, T
Format: Article
Language:English
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Summary:The parameter optimization study for the desymmetrization of meso-cyclopenten-1,4-diol 1 through irreversible transesterification using an immobilized lipase from Mucor meihei, i.e., Lipozyme ®/Chirazyme ® is presented. The enzyme was studied for the transesterification of 1 in various organic solvents by varying reaction parameters such as the nature of acyl donor, temperature, enzyme quantity etc., to afford optically active 4-( R)-hydroxycyclopent-2-en-1-( S)-acetate 2 of >98% enantiomeric excess in >60% yield.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00068-3