ICCAS OpenIR
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
Wang, MX; Zhao, SM
2002-08-14
Source PublicationTETRAHEDRON-ASYMMETRY
ISSN0957-4166
Volume13Issue:15Pages:1695-1702
AbstractIn 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.
Indexed ByIC ; CCR ; SCI
Language英语
WOS IDWOS:000178048300016
PublisherPERGAMON-ELSEVIER SCIENCE LTD
Citation statistics
Cited Times:36[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/78342
Collection中国科学院化学研究所
Corresponding AuthorWang, MX
AffiliationChinese Acad Sci, Ctr Mol Sci, Inst Chem, Beijing 100864, Peoples R China
Recommended Citation
GB/T 7714
Wang, MX,Zhao, SM. 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[J]. TETRAHEDRON-ASYMMETRY,2002,13(15):1695-1702.
APA Wang, MX,&Zhao, SM.(2002).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.TETRAHEDRON-ASYMMETRY,13(15),1695-1702.
MLA Wang, MX,et al."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".TETRAHEDRON-ASYMMETRY 13.15(2002):1695-1702.
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