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  • Title: Hammett correlation of nornicotine analogues in the aqueous aldol reaction: implications for green organocatalysis.
    Author: Rogers CJ, Dickerson TJ, Brogan AP, Janda KD.
    Journal: J Org Chem; 2005 Apr 29; 70(9):3705-8. PubMed ID: 15845010.
    Abstract:
    [reaction: see text] 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 rho = 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 organo-catalyst.
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