Diametric Stereoselectivity of Pseudomonas fluorescens Lipase and Candida cylindracea Lipase in the Acylation of Organometallic Alcohols

Abstract

The monoacylation of (η⁶-1, 2-benzenedimethanol)tricarbonylchromium (2) by vinyl acetate, palmitate and benzoate, alcoholysis of the corresponding diesters of 2 in n-butanol, and acylation of (η⁶-benzyl alcohol) tricar bonylchromium by (±)-vinyl 2-phenoxypropanoate and 2-phenylpropanoate were accomplished with lipase P (from P. fluorescens) and lipase CC (from C. cylindracea) to give optically active organometallic esters. Their configurations indicated that the Stereoselectivity of each of these two Upases was in marked contrast. An active site model for them is proposed.