Rogers Claude J, Dickerson Tobin J, Brogan Andrew P, Janda Kim D
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
J Org Chem. 2005 Apr 29;70(9):3705-8. doi: 10.1021/jo050161r.
[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.
[反应：见正文] 合成了一系列间位和对位取代的2-芳基吡咯烷，并考察了它们在缓冲条件下催化水相羟醛反应的能力。芳基吡咯烷催化反应的动力学分析显示出线性哈米特相关性，ρ = 1.14（R² = 0.996），表明吸电子芳环可加速该反应。这些结果为开发一种合成上可行的水相有机催化剂带来了希望。
