title: Regio- and stereoselective oxidation of unactivated C-H bonds with Rhodococcus rhodochrous.
abstract: 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.
authors.affiliation: School of Chemistry, Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester, M1 7ND, UK, , Tel: +44 (0)161 3065172.
authors.forename: Elaine
authors.initials: E
authors.lastname: O'Reilly
authors.forename: Suzanne J
authors.initials: SJ
authors.lastname: Aitken
authors.forename: Gideon
authors.initials: G
authors.lastname: Grogan
authors.forename: Paul P
authors.initials: PP
authors.lastname: Kelly
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Turner
authors.forename: Sabine L
authors.initials: SL
authors.lastname: Flitsch