Journal of the American Chemical Society

Catalytic regioselectivity control in ring-opening cycloisomerization of methylene-or alkylidenecyclopropyl ketones

S Ma, L Lu, J Zhang

Index: Ma, Shengming; Lu, Lianghua; Zhang, Junliang Journal of the American Chemical Society, 2004 , vol. 126, # 31 p. 9645 - 9660

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Citation Number: 122

Abstract

2-Methylene-or alkylidenecyclopropanyl ketones were easily prepared by the regioselective cyclopropanation of allenes or the reaction of methylene-/alkylidenecyclopropanyllithium with N, N-dimethyl carboxylic acid amides. Due to the presence of the exo-cyclic CC bond and the strained cyclopropane, their highly selective ring-opening cycloisomerization using PdCl2 (CH3CN) 2, NaI (or PdCl2 (CH3CN) 2+ NaI), and Pd (PPh3) 4 as catalysts provided ...