Nitrile biotransformations for the synthesis of enantiomerically enriched Baylis–Hillman adducts

文献情報

出版日 2002-12-23

DOI 10.1039/B209791E

インパクトファクター 3.876

著者

Mei-Xiang Wang, Yan Wu

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要旨

Catalysed by the nitrile hydratase/amidase-containing Rhodococcus sp. AJ270 cells, a number of β-aryl- and β-alkyl- β-hydroxy-α-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 β-position of the substrates. The protection of the free hydroxy of β-phenyl-β-hydroxy-α-methylenepropiononitrile 1a by methylation led to the enhancement of enantiocontrol of the biohydrolysis.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Nitrile biotransformations for the synthesis of enantiomerically enriched Baylis–Hillman adducts

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