Synergistic effects within a C 2-symmetric organocatalyst: the potential formation of a chiral catalytic pocket

…, HL Brozinski, LC Henderson

Index: Delaney, Joshua P.; Brozinski, Hannah L.; Henderson, Luke C. Organic and Biomolecular Chemistry, 2013 , vol. 11, # 18 p. 2951 - 2960

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Citation Number: 7

Abstract

This study describes the synthesis of five novel C2-symmetric organocatalysts that facilitate the on-water asymmetric aldol reaction at low catalyst loading (1 mol%) without the use of additives. Each catalyst is composed of two diprolinamide units joined by a symmetric alkyl bridging group allowing for systematic modulation of catalytic site proximity. Typically, catalysts in this manuscript which bear the catalytic units in close proximity gave the best ...