53313-48-7Relevant academic research and scientific papers
Ammonium-directed oxidation of cyclic allylic and homoallylic amines
Bond, Christopher W.,Cresswell, Alexander J.,Davies, Stephen G.,Fletcher, Ai M.,Kurosawa, Wataru,Lee, James A.,Roberts, Paul M.,Russell, Angela J.,Smith, Andrew D.,Thomson, James E.
, p. 6735 - 6748 (2009)
(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.
