Ammonium-directed oxidation of cyclic allylic and homoallylic amines

…, SG Davies, AM Fletcher, W Kurosawa…

Index: 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. Journal of Organic Chemistry, 2009 , vol. 74, # 17 p. 6735 - 6748

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Citation Number: 52

Abstract

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 ( ...