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

• Main Authors: Elaine O’Reilly, Suzanne J. Aitken, Gideon Grogan, Paul P. Kelly, Nicholas J. Turner, Sabine L. Flitsch
• Format: Article
• Language: English
• Published: Beilstein-Institut 2012-04-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: biocatalysis; cytochrome P450; hydroxylation; Rhodococcus rhodochrous; selective C–H activation
• Online Access: https://doi.org/10.3762/bjoc.8.56

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.