Hammett correlation of nornicotine analogues in the aqueous aldol reaction: implications for green organocatalysis

CJ Rogers, TJ Dickerson, AP Brogan…

Index: Rogers, Claude J.; Dickerson, Tobin J.; Brogan, Andrew P.; Janda, Kim D. Journal of Organic Chemistry, 2005 , vol. 70, # 9 p. 3705 - 3708

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Citation Number: 45

Abstract

A series of meta-and para-substituted 2-arylpyrrolidines were synthesized and examined for their ability to catalyze an aqueous aldol reaction under buffered conditions. Kinetic analysis of arylpyrrolidine-catalyzed reactions displayed a linear Hammett correlation with ρ= 1.14 (R 2= 0.996), indicating that the reaction is accelerated by electron-withdrawing aryl rings. These results show promise for the development of a synthetically viable aqueous ...