Organic letters

Converting gem-Dimethyl Groups into Cyclopropanes via Pd-Catalyzed Sequential CH Activation and Radical Cyclization

R Giri, M Wasa, SP Breazzano, JQ Yu

Index: Giri, Ramesh; Wasa, Masayuki; Breazzano, Steven P.; Yu, Jin-Quan Organic Letters, 2006 , vol. 8, # 25 p. 5685 - 5688

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Citation Number: 52

Abstract

A novel route to the synthesis of cyclopropane derivatives is described. 1, 1-Dimethyls in 2- (1, 1-dimethylalkyl) dimethyloxazolines are first converted into 1, 3-diiodide derivatives via Pd-catalyzed sequential CH activation and then radically cyclized to provide 2-(1- alkylcylclopropyl) dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.