Benzylidene succinimides as 3C synthons for the asymmetric tandem Mannich reaction/transamidation of cyclic trifluoromethyl ketimines to obtain F < sub > 3 < /sub > C-containing polycyclic dihydroquinazolinones

Chem Commun (Camb). 2021 Feb 23. doi: 10.1039/d0cc08131k. Online ahead of print.ABSTRACTBy taking advantage of benzylidene succinimides as a new class of 3C synthons, a highly diastereo- and enantioselective tandem Mannich reaction/transamidation has been established by reacting them with cyclic trifluoromethyl N-acyl ketimines. Using a Cinchona alkaloid-derived squaramide as the catalyst, the tandem reaction proceeded smoothly under mild conditions and afforded a range of F3C-containing chiral polycyclic dihydroquinazolinones with excellent results (up to 99% yield, all cases >20 : 1 dr, up to 99% ee).PMID:33620365 | DOI:10.1039/d0cc08131k

Source: Chemical Communications - February 23, 2021 Category: Chemistry Authors: Xia-Yan Zhang Pei-Hao Dou Wen-Ya Lu Yong You Jian-Qiang Zhao Zhen-Hua Wang Wei-Cheng Yuan Source Type: research