Asymmetric Vinylogous Aldol Reaction of Silyloxy Furans with a Chiral Organic Salt

Despite their synthetic significance there is a general lack of asymmetric vinylogous aldol reactions that tolerate variations of both the silyloxy furans and aldehydes. We have developed a new chiral organic catalyst based on a carboxylate-ammonium salt prepared from a thiourea-amine and a carboxylic acid. This new catalyst enabled us to develop an efficient asymmetric vinylogous aldol reaction of unprecedented scope with respect to both 2-trimethylsilyloxy furans and aldehydes.

尽管这类反应具有重要的合成应用价值，但目前普遍缺乏能够同时兼容硅氧基呋喃与醛类底物结构变化的不对称插烯羟醛反应体系。我们开发了一种新型手性有机催化剂，该催化剂由硫脲-胺与羧酸反应制得的羧酸铵盐构建而成。该新型催化剂助力我们开发出一种高效的不对称插烯羟醛反应，其针对2-三甲基硅氧基呋喃与醛类两类底物均展现出前所未有的底物适用范围。