A versatile catalyst for asymmetric reactions of carbonyl groups working purely by activation through hydrogen bonding: Mukaiyama-aldol,hetero Diels-Alder and Friedel-Crafts reactions

摘要

Bis-sulfonamides are demonstrated to be promising candidates for the efficient activation of carbonyl compounds through hydrogen bonding.Exemplified by three carbonyl addition reactions: Mukaiyama-aldol,hetero Diels-Alder and Friedel-Crafts reactions we show that bis-triflamides or bis-nonaflamides of commercially available chiral diamines act as chiral Bronsted-acid catalysts,leading to the optically active products in moderate to excellent yields and with enantioselectivities up to 73% ee.