Solvent-dependent chemoselectivities in additions of β-carbonyl imines to allyltrimethylsilane with CTAN

Y Zhang, AJ Raines, RA Flowers

Index: Zhang, Yang; Raines, Andrew J.; Flowers II, Robert A. Journal of Organic Chemistry, 2004 , vol. 69, # 19 p. 6267 - 6272

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Citation Number: 30

Abstract

The oxidative coupling of β-carbonyl imines and allyltrimethylsilane with CTAN were investigated in CH3CN and CH2Cl2. In CH3CN allylation products were obtained predominantly, while in CH2Cl2, dihydropyrrole products were obtained exclusively. Solvent- assisted nucleophilic cleavage of the intermediate β-silyl cation is proposed to play a role in the solvent-dependent chemoselectivity.