Synthesis of enantiomerically enriched (S)-(+)-2-aryl-4-pentenoic acids and (R)-(-)-2-aryl-4-pentenamides via microbial hydrolysis of nitriles, a chemoenzymatic approach to stereoisomers of alpha,gamma-disubstituted gamma-butyrolactones

摘要

In the presence of the nitrile hydratase amidase-containing Rhodococcus sp. AJ270 whole cell catalyst. 2-aryl-4-pentenenitriles 1 underwent enantioselective hydrolysis under mild conditions to afford (R)-(-)-2-aryl-4-pentenoic acid amides 2 and (S)-(+)-2-aryl-4-pentenoic acids 3 in almost quantitative yield. The amidase involved in the cells shows very high S-enantioselectivity whereas the nitrite hydratase exhibits low to moderate S-enatitioselectivity. The synthesis of stereoisomers of chi,gamma-disubstituted gamma-butyrolactones from iodolactonization of (S)-(+)-2-aryl-4-pentenoic acid was demonstrated. (C) 2002 Elsevier Science Ltd. All rights reserved. [References: 28]