T. Schirmeister et Hh. Otto, ENZYME-CATALYZED HYDROLYZES OF E Z-DIASTEREOTOPIC AND E/Z-DIASTEREOMERIC ESTERS - AFFECT ON SELECTIVITY BY REACTION MEDIA/, Journal of organic chemistry, 58(18), 1993, pp. 4819-4822
PLE-catalyzed hydrolyses of different types of E/Z-diastereotopic dies
ters and E/Z-diastereomeric monoesters have been studied. Arylidenepro
panedioic diesters are specifically hydrolyzed to the Z-half esters, w
hereas the de values for dialkylated methylene propanedioic diesters r
ange between 33 and 79% (Z). D values for the hydrolyses of the 3-meth
yleneazetidin-2-ones in detergent-buffer systems depend on the size of
the substituent in the alpha-position. Diastereoselectivity of these
substrates is affected by addition of the cosolvents acetonitrile and
methanol.