The α-effect in iminium ion catalysis

JL Cavill, RL Elliott, G Evans, IL Jones, JA Platts…

Index: Cavill, Julie L.; Elliott, Richard L.; Evans, Gareth; Jones, Ian L.; Platts, James A.; Ruda, Antonio M.; Tomkinson, Nicholas C. O. Tetrahedron, 2006 , vol. 62, # 2-3 p. 410 - 421

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Citation Number: 53

Abstract

The α-effect can be used as an effective means to promote iminium ion catalysed transformations, providing acyclic scaffolds to aid in catalyst design. A thorough investigation of the structure–activity relationship of the catalyst architecture reveals optimal substituents of a disubstituted carbamate and a secondary alkyl group around a hydrazine scaffold. Molecular modelling investigations provide a mechanistic rationale to the results observed.