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 α,γ-disubstituted γ-butyrolactones
2002; Elsevier BV; Volume: 13; Issue: 15 Linguagem: Inglês
10.1016/s0957-4166(02)00470-6
ISSN1362-511X
AutoresMei‐Xiang Wang, Shengmin Zhao,
Tópico(s)Cyclopropane Reaction Mechanisms
ResumoIn 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 nitrile hydratase exhibits low to moderate S-enantioselectivity. The synthesis of stereoisomers of α,γ-disubstituted γ-butyrolactones from iodolactonization of (S)-(+)-2-aryl-4-pentenoic acid was demonstrated.
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