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Utilizing hydrolases of opposite enantiopreference for the preparation of both enantiomers of (1 R ,7a R )‐(−)‐ and (1 S ,7a S )‐(+)‐3,6,7,7a‐tetrahydro‐1‐hydroxy‐7a‐methyl‐1 H ‐inden‐5(2 H )‐one
Author(s) -
Lo LeeChiang,
Chou TzyyChao,
Shie JungJing
Publication year - 2004
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20023
Subject(s) - chemistry , candida rugosa , enantiomer , lipase , hydrolysis , substrate (aquarium) , chirality (physics) , enantiomeric excess , stereochemistry , organic chemistry , enzyme , enantioselective synthesis , chromatography , catalysis , chiral symmetry , oceanography , nambu–jona lasinio model , physics , quantum mechanics , quark , geology
Four racemic esters of (1 R *,7a R *)‐3,6,7,7a‐tetrahydro‐1‐hydroxy‐7a‐methyl‐1 H ‐inden‐5(2 H )‐one were prepared and subjected to hydrolysis with two types of hydrolases, including alcalase and three lipases. Alcalase and lipase showed opposite enantiopreference on these esters. Based on this result, we developed a gram‐scale procedure using butanoate as the substrate, which was treated consecutively with alcalase and lipase from Candida rugosa (CRL), to give both enantiomers of the title compound in high yields and high enantiomeric excess. Chirality 16:267–271, 2004. © 2004 Wiley‐Liss, Inc.