Synthesis of novel chiral 1,3-aminophenols and application for the enantioselective addition of diethylzinc to aldehydes
作者:Xiao-Feng Yang、Zhao-Hui Wang、Tomoaki Koshizawa、Mikio Yasutake、Guang-You Zhang、Takuji Hirose
DOI:10.1016/j.tetasy.2007.05.027
日期:2007.6
Novel chiral 1,3-aminophenols were efficiently synthesized by applying a Friedel-Crafts reaction and optical resolution. The catalytic activity of the aminophenols was studied for the addition of diethylzinc to benzaldehyde. The results showed that (S)-5a with bulky tert-butyl groups on the stereogenic carbon atom and 4,6-positions of phenol favored higher enantio selectivity (94% ee). The same ligand was also used with other aldehydes, to give optically active alcohols in good chemical yields and cc values (up to 99%). (C) 2007 Elsevier Ltd. All rights reserved.