title: Hammett correlation of nornicotine analogues in the aqueous aldol reaction: implications for green organocatalysis.
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.
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Claude J
authors.initials: CJ
authors.lastname: Rogers
authors.forename: Tobin J
authors.initials: TJ
authors.lastname: Dickerson
authors.forename: Andrew P
authors.initials: AP
authors.lastname: Brogan
authors.forename: Kim D
authors.initials: KD
authors.lastname: Janda
mesh_terms: 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
chemical_list: D007202:Indicators and Reagents; D011759:Pyrrolidines; D014867:Water; D009538:Nicotine; C005311:nornicotine