The first synthesis of both enantiomers of 2-hydroxycyclobutanone acetals by enzymatic transesterification: preparation of (R)-(+)-2-benzyloxycyclobutanone and its antipode

摘要

A new practical enzymatic synthesis of (R)-(+)- and (S)-(-)-2-acetoxycyclobutanone acetals with 97-99.9% ee has been carried out via enzymatic transesterification of readily available racemic 2-hydroxycyclobutanone acetals. The absolute configuration has been established by X-ray analysis of the corresponding (S)-naproxenyl derivative. The first preparation of enantiomerically pure (R)-(+)- and (S)- (-)-2- benzyloxycyclobutanones was accomplished by means of protection of the hydroxy group followed by deacetalation reaction. (C) 2004 Elsevier Ltd. All rights reserved.