PRODUCTION OF 3-HYDROX-4-SULFENYL-SUBSTITUTED ACETOACETIC ACID ESTER

摘要

PROBLEM TO BE SOLVED: To obtain the subject optically active compound especially useful as an intermediate for aβ-lactam compound by reducing 4-sulfenyl-substituted acetoacetic acid ester with baker's yeast in the presence of a specific compound, thereby proceeding the reaction in a short time. SOLUTION: An optically active 3-hydroxy-4-sulfenyl-substituted acetoacetic acid ester of the formula II is produced by reducing a 3-oxo-4-sulfenyl-substituted acetoacetic acid ester of the formula I (R<1> is phenyl or a phenylalkyl; R<2> is an alkyl) with baker's yeast in the presence of saccharose. A reduction product can be produced in high enanthio-selectivity by the reduction of an acetoacetic acid ester derivative having sulfenyl group at the 4-site. Especially, an optically pure reduction product of R isomer is produced by using ethyl 4- phenylthioacetoacetate. The reduction product can be converted intoβ- hydroxyamide and induced to aβ-lactam compound by photo-extension reaction.