Aziridin-2-yl methanols as organocatalysts in Diels-Alder reactions and Friedel-Crafts alkylations of N-methyl-pyrrole and N-methyl-indole

作者：Bonini Bianca F^*; Capito Elena; Comes Franchini Mauro; Fochi Mariafrancesca; Riccia Alfredo; Zwanenburg Binne

来源：Tetrahedron: Asymmetry , 2006, 17(22): 3135-3143.

DOI：10.1016/j.tetasy.2006.11.028

A series of enantiomerically pure aziridin-2-yl methanols have been synthesized from aziridine-2-carboxylic esters and have been tested as organocatalysts in Diels-Alder reactions and Friedel-Crafts alkylations of N-methyl-pyrrole and N-methyl-indole using alpha,beta-unsaturated aldehydes. Moderate to good ee's have been obtained. The coupling of N-methyl-pyrrole with crotonaldehyde and cinnamaldehyde using (2S,3S)-3-methylazirin-2-yl(diphenyl)methanol TFA salt as the catalyst gave the best results (ee 75%).

• 出版日期2006-11-27