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From the same journal

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

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Published copy (DOI)

Author(s)

  • E. O'Reilly
  • S.J. Aitken
  • P.P. Kelly
  • N.J. Turner
  • S.L. Flitsch
  • G. Grogan

Department/unit(s)

Publication details

JournalBeilstein Journal of Organic Chemistry
DatePublished - 3 Apr 2012
Volume8
Pages (from-to)496-500
Original languageEnglish

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.

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