ICCAS OpenIR
Nitrile biotransformations for the synthesis of enantiomerically enriched Baylis-Hillman adducts
Wang, MX; Wu, Y
2003-02-07
Source PublicationORGANIC & BIOMOLECULAR CHEMISTRY
ISSN1477-0520
Volume1Issue:3Pages:535-540
AbstractCatalysed by the nitrile hydratase/amidase-containing Rhodococcus sp. AJ270 cells, a number of beta-aryl- and beta-alkyl-beta-hydroxy-alpha-methylenepropiononitriles (the Baylis-Hillman nitriles) 1 underwent hydrolysis under mild conditions to produce the corresponding enantiomerically enriched Baylis-Hillman amides 2 and acids 3. The enantioselectivity of the biotransformations was strongly determined by the steric effect of the substituents at the beta-position of the substrates. The protection of the free hydroxy of beta-phenyl-beta-hydroxy-alpha-methylenepropiononitrile 1a by methylation led to the enhancement of enantiocontrol of the biohydrolysis.
DOI10.1039/b209797e
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000181670100018
PublisherROYAL SOC CHEMISTRY
Citation statistics
Cited Times:39[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/81244
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,Wu, Y. Nitrile biotransformations for the synthesis of enantiomerically enriched Baylis-Hillman adducts[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2003,1(3):535-540.
APA Wang, MX,&Wu, Y.(2003).Nitrile biotransformations for the synthesis of enantiomerically enriched Baylis-Hillman adducts.ORGANIC & BIOMOLECULAR CHEMISTRY,1(3),535-540.
MLA Wang, MX,et al."Nitrile biotransformations for the synthesis of enantiomerically enriched Baylis-Hillman adducts".ORGANIC & BIOMOLECULAR CHEMISTRY 1.3(2003):535-540.
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