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

Claude J Rogers Tobin J Dickerson Andrew P Brogan Kim D Janda

J Org Chem

Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Published: April 2005

[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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http://dx.doi.org/10.1021/jo050161rDOI Listing

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