Tetrahedron Asymmetry p. 1437 - 1448 (1996)
Update date:2022-08-06
Topics:
Egri, Gabriella
Baitz-Gacs, Eszter
Poppe, Laszlo
Enantiomer selectivity of lipase catalyzed acylation of 2-acylated 1,2-diols was studied. First, acylation of 2-acetoxyheptan-1-ol rac-3b with vinyl acetate was investigated by varying the enzymes and the solvent, showing the highest enantiomer selectivity by using lipase from Pseudomonas fluorescens (PfL) in hexane-vinyl acetate (VA). We have found varying or even reversed enantiomer selectivity for different secondary acyl moieties in 2-acyloxyheptan-1-ols rac-3bA-F. Next, all six possible types of enantiomer selective biotransformations (hydrolysis of diacetate and the two kinds of monoacetetes; acylation of diol and the two kinds of monoacetates) were compared on two model diols rac-4b,d. Among the transformations investigated, acetylation of secondary monoacetates rac-3b,d showed the highest enantiomer selectivity. Finally, PfL catalyzed acetylations of several 2-acetylated 1,2-diols rac-3a-g were investigated under our optimum conditions.
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Doi:10.1016/0022-328X(95)06081-7
(1996)Doi:10.1021/acs.joc.7b03176
(2018)Doi:10.1007/s11164-014-1857-5
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(1996)