Tetrahedron letters

The carbonyl epoxide rearrangement. Epoxy imines in the formation of heterotropane derivatives.

HH Wasserman, M Thyes, S Wolff, V Rusiecki

Index: Wasserman, Harry H.; Thyes, Marco; Wolff, Steven; Rusiecki, Victoria Tetrahedron Letters, 1988 , vol. 29, # 39 p. 4973 - 4976

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Citation Number: 6

Abstract

Abstract The carbonyl epoxide rearrangement can be extended to δ, ε-epoxy imines. The reaction takes place by intramolecular nucleophilic displacement involving attack of the imino nitrogen on the epoxide ring. A high degree of stereospecificity is observed in this process which provides a facile route to 6-oxa-8-azabicyclo [3.2. 1] octanes.