The first enzymatic desymmetrizations of prochiral phosphine oxides
摘要:
Prochiral bis(methoxycarbonylmethyl)phenylphosphine oxide was subjected to PLE-mediated hydrolysis to give a chiral monoacetate in 92% yield and 72% e.e. In turn, prochiral bis(hydroxymethyl)phenylphosphine oxide was desymmetrized, using either a lipase-catalyzed acetylation or hydrolysis of the corresponding diacetyl derivative, to give a chiral monoacetate in the yield up to 76% and with e.e.s up to 79%. Absolute configurations of the products were determined by means of chemical correlation. (C) 2003 Elsevier Ltd. All rights reserved.