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Rearrangement of chiral 1-bromo-N-nitrobicyclo[2.2.1]heptan-2-imines

Authors
Publisher
Elsevier Ltd
Publication Date
Volume
24
Identifiers
DOI: 10.1016/j.tetasy.2013.06.001

Abstract

Abstract The regio- and diastereospecific Wagner-Meerwein-type rearrangements of the potassium cyanide adducts of camphor-derived substituted 1-bromo-N-nitrobicyclo[2.2.1]heptan-2-imines under acidic conditions have been investigated. The selective formation of bromonorbornene derivatives has been demonstrated in the case of rearrangements involving intermediate α-bromocarbocations containing vicinal hydrogen atoms. In all other cases, hydrolysis of the intermediates resulted in the formation of a carbonyl group. The simplicity of this transformation opens up a novel and straightforward synthetic pathway to enantiopure derivatives of bridgehead-substituted norbornane carboxamides in just three steps, starting from 1-bromonorbornanones.

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