Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrous

Beilstein Journal of Organic Chemistry

Gideon Grogan¹  Elaine O’Reilly²  Sabine L. Flitsch²  Paul P. Kelly²  Nicholas J. Turner²  Suzanne J. Aitken² 

[1] Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK, Tel: [phone];School of Chemistry, Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester, M1 7ND, UK, Fax: [phone], Tel: [phone];

关键词: biocatalysis;    cytochrome P450;    hydroxylation;    Rhodococcus rhodochrous;    selective C–H activation;   

DOI  :  10.3762/bjoc.8.56

来源: DOAJ

【 摘 要 】

The ability of Rhodococcus rhodochrous (NCIMB 9703) to catalyse the regio- and stereoselective hydroxylation of a range of benzyloxy-substituted heterocycles has been investigated. Incubation of 2-benzyloxytetrahydropyrans with resting cell suspensions of the organism yielded predominantly a mixture of 5-hydroxylated isomers in combined yields of up to 40%. Exposure of the corresponding 2-benzyloxytetrahydrofuran derivatives to the cell suspensions gave predominantly the 4-hydroxylated isomers in yields of up to 26%. Most interestingly, 2-(4-nitrobenzyloxy)tetrahydrofuran and 2-(4-nitrobenzyloxy)tetrahydropyran were transformed in high yields to the 4-hydroxylated and 5-hydroxylated products, respectively.

【 授权许可】

Unknown