Rearrangement of ammonium ylides produced by intramolecular reaction of catalytically generated metal carbenoids. Part 2. Stereoselective synthesis of bicyclic …

…, PB Hodgson, MD Goldsmith, AJ Blake…

Index: Clark; Hodgson; Goldsmith; Blake; Cooke; Street Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 24 p. 3325 - 3337

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Citation Number: 39

Abstract

Ammonium ylides produced by intramolecular reaction of copper carbenoids tethered to cyclic allylic amines undergo [2,3]-rearrangement to deliver bicyclic amines. The reaction can be performed using a cyclic N-allylamine in which the diazo group is tethered adjacent to nitrogen, or a vinyl-substituted cyclic amine in which the diazo group is N-tethered to the ring. In the former type of reaction, stereoselective ylide formation and rearrangement usually delivers high ...