Rearrangement of ammonium ylides produced by intramolecular reaction of catalytically generated metal carbenoids. Part 1. Synthesis of cyclic amines

…, PB Hodgson, MD Goldsmith, LJ Street

Index: Clark; Hodgson; Goldsmith; Street Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 24 p. 3312 - 3324

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Citation Number: 35

Abstract

Cyclic amines have been prepared in good yield by [2, 3]-rearrangement of ammonium ylides produced by intramolecular reaction of copper carbenoids tethered to allylic amines. Copper (II) acetylacetonate is the optimum catalyst for carbenoid/ylide generation from the diazo ketone precursor, and reactions must be performed at elevated temperatures in order to obtain reasonable reaction rates and high yields. The reaction has been used to ...