Chiral synthon obtained with pig liver esterase: introduction of chiral centers into cyclohexene skeleton.
A versatile chiral synthon, (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid, was obtained by an enantioselective hydrolysis of the corresponding meso diester with pig liver esterase. This enzymatic hydrolysis can easily be carried out on a multi-hundred gram scale. The chiral monoester thus obtained can be further converted into all stereoisomers of 1-amino-2-alkoxycarbonyl-4-cyclohexene derivatives in an enantio- and stereocontrolled manner. These derivatives are considered as potential key intermediates for synthesizing a variety of biologically interesting compounds such as aminocyclitol and carbapenem antibiotics.
Kobayashi
S
S
Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.
Kamiyama
K
K
Ohno
M
M
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003509:Cyclohexanecarboxylic Acids; D003510:Cyclohexanes / Q000032:analysis*; D053138:Cyclohexenes; D004950:Esterases / Q000378:metabolism*; D008099:Liver / Q000201:enzymology*; D013237:Stereoisomerism; D013552:Swine
D003509:Cyclohexanecarboxylic Acids; D003510:Cyclohexanes; D053138:Cyclohexenes; C052568:cyclohexene; C064173:6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid; D004950:Esterases