Hammett correlation of nornicotine analogues in the aqueous aldol reaction: implications for green organocatalysis.
[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.
Rogers
Claude J
CJ
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Dickerson
Tobin J
TJ
Brogan
Andrew P
AP
Janda
Kim D
KD
D002384:Catalysis; D007202:Indicators and Reagents; D007700:Kinetics; D015394:Molecular Structure; D009538:Nicotine / Q000031:analogs & derivatives* / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D007202:Indicators and Reagents; D011759:Pyrrolidines; D014867:Water; D009538:Nicotine; C005311:nornicotine