ICCAS OpenIR
Nitrile biotransformation for highly enantioselective synthesis of 3-substituted 2,2-dimethylcyclopropanecarboxylic acids and amides
Wang, MX; Feng, GQ
2003-01-24
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume68Issue:2Pages:621-624
AbstractBiotransformations of differently configured 2,2dimethyl-3-substitued-cyclopropanecarbonitriles were studied using a nitrile hydratase/amidase-containing Rhodococcus sp. AJ270 whole-cell catalyst under very mild conditions. Although all of the cis-3-aryl-2,2-dimethylcyclopropanecarbonitriles appeared inert toward the biocatalyst, a number of racemic trans-isomers efficiently underwent a highly enantioselective hydrolysis to produce (+)-(1R,3R)-3-aryl-2,2-dimethylcyclopropanecarboxylic acids and (-)-(1S,3S)3-aryl-2,2-dimethyleyclopropanecarboxamides in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the biotransformations of nitriles originated from the combined effects of 1R-enantioselective nitrile hydratase and amidase, with the later being a dominant factor. The influence of the substrates on both reaction efficiency and enantioselectivity was discussed in terms of steric and electronic effects. Coupled with chemical transformations, biotransformations of nitriles provided convenient syntheses of optically pure geminally dimethylsubstituted cyclopropanecarboxylic acids and amides, including chrysanthemic acids, in both enantiomeric forms.
DOI10.1021/jo026490q
Indexed BySCI ; CCR
Language英语
WOS IDWOS:000180540500056
PublisherAMER CHEMICAL SOC
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Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/79928
Collection中国科学院化学研究所
Corresponding AuthorWang, MX
AffiliationChinese Acad Sci, Inst Chem, Ctr Mol Sci, Biol Chem Lab, Beijing 100080, Peoples R China
Recommended Citation
GB/T 7714
Wang, MX,Feng, GQ. Nitrile biotransformation for highly enantioselective synthesis of 3-substituted 2,2-dimethylcyclopropanecarboxylic acids and amides[J]. JOURNAL OF ORGANIC CHEMISTRY,2003,68(2):621-624.
APA Wang, MX,&Feng, GQ.(2003).Nitrile biotransformation for highly enantioselective synthesis of 3-substituted 2,2-dimethylcyclopropanecarboxylic acids and amides.JOURNAL OF ORGANIC CHEMISTRY,68(2),621-624.
MLA Wang, MX,et al."Nitrile biotransformation for highly enantioselective synthesis of 3-substituted 2,2-dimethylcyclopropanecarboxylic acids and amides".JOURNAL OF ORGANIC CHEMISTRY 68.2(2003):621-624.
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