Ammonium-directed oxidation of cyclic allylic and homoallylic amines

Christopher W. Bond, Alexander J. Cresswell, Stephen G. Davies, Ai M. Fletcher, Wataru Kurosawa, James A. Lee, Paul M. Roberts, Angela J. Russell, Andrew D. Smith, James E. Thomson

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58 Citations (Scopus)

Abstract

(Chemical Equation Presented) The ammonium-directed olefinic oxidation of a range of cyclic allylic and homoallylic amines has been investigated. Functionalization of a range of allylic 3-(N,N-dibenzylamino)cycloalk-1-enes with m-CPBA in the presence of Cl3CCO2H gives exclusively the corresponding syn-epoxide for the 5-membered ring (>99:1 dr), the anti-epoxide for the 8-membered ring (>99:1 dr), and predominantly the anti-epoxide for the 7-membered ring (94:6 dr). Oxidation of the homoallylic amines 3-(Nbenzylamino) methylcyclohex-1-ene and 3-(N,N-dibenzylamino)methylcyclohex-1-ene gave, in both cases, the correspondingN-protected 1,2-anti-2,3-syn-3-aminomethylcyclohexane- 1,2-diol with high levels of diastereoselectivity (g90:10 dr). The versatile synthetic intermediates resulting from these oxidation reactions are readily transformed into a range of amino diols.

Original languageEnglish
Pages (from-to)6735-6748
Number of pages14
JournalJournal of Organic Chemistry
Volume74
Issue number17
DOIs
Publication statusPublished - 4 Sep 2009

ASJC Scopus subject areas

  • Organic Chemistry

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