ENANTIOFACIAL SELECTIVE REDUCTION OF 2-ALLYL-2-CARBOETHOXY-CYCLOPENTANONE MEDIATED BY BAKERS-YEAST

Enantioselective reduction of 2-allyl-2-carboethoxy-cyclopentanone (2) was accomplished in high enantiomeric excess (> 99%), using baker's y east in the presence of CuO, to obtain the (+)-2-allyl-2-carboethoxy-c yclopentanol derivative (6). This methodology also provides an entry t o corresponding beta-keto ester (-)-(2), representing an important str ategy to prepare chiral functionalized 2-oxabicyclic[3.3.0]octane and 2-oxabicyclic[4.4.0]nonane derivatives, useful synthons to access new bioactive compounds. (C) 1996 Wiley-Liss, Inc.