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Chemoenzymatic approach to optically active phenylglycidates: resolution of bromo- and iodohydrins

IR@CSIR-IIIM

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Title Chemoenzymatic approach to optically active phenylglycidates: resolution of bromo- and iodohydrins
 
Creator Anand, Naveen
Kapoor, Munish
Koul, Surrinder
Taneja, Subhash C.
Sharma, Rattan L.
Qazi, Ghulam N.
 
Subject Chemical Sciences
 
Description Enantiomerically enriched phenylglycidates, precursors of the taxol C-13 phenylisoserine side chain and diltiazem, were prepared by kinetic resolution of anti-2-bromo-3-hydroxy- and anti-3-hydroxy-2-iodophenylpropanoates to provide enantioriched(2R,3R)- and (2S,3S)-halohydrins. The bulkiness and inflexibility of bromo and iodo groups in halohydrins have made them inaccessible to the active site of most of the lipases utilized for the hydrolysis of their acyloxy derivatives. In a set of 22 hydrolases screened herein,including native as well as commercial enzymes, only Aspergillus niger (Lipase AS, AMANO) could catalyze the hydrolysis with high enantioselectivity (E = 176). The resolved halohydrins easily underwent transformation to the corresponding (2S,3R)- and (2R,3S)-phenylglycidates.
 
Date 2004
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://iiim.csircentral.net/229/1/10.1016j.tetasy.2004.08.026.pdf
Anand, Naveen and Kapoor, Munish and Koul, Surrinder and Taneja, Subhash C. and Sharma, Rattan L. and Qazi, Ghulam N. (2004) Chemoenzymatic approach to optically active phenylglycidates: resolution of bromo- and iodohydrins. Tetrahedron: Asymmetry, 15 (19). pp. 3131-3138. ISSN 09574166
 
Relation http://dx.doi.org/10.1016/j.tetasy.2004.08.026
http://iiim.csircentral.net/229/