Asymmetric Synthesis of CF3- and Indole-Containing Thiochromanes via a Squaramide-Catalyzed Michael–Aldol Reaction

• DOI: 10.1021/acs.orglett.6b01498
• Publication Date: 2016-07-08T12:48:26Z
• Authors: Yuanyuan Zhu; Zhenghao Dong; Xin Cheng; Xiaoling Zhong; Xiaolin Liu; Li Lin; Zhiqiang Shen; Peiju Yang; Yuan Li; Hailin Wang; Wenjin Yan; Kairong Wang; Rui Wang
• Keywords: 01 natural sciences; 3. Good health; 0104 chemical sciences

A Michael-aldol reaction of 2-mercaptobenzaldehyde with β-indole-β-CF3 enones catalyzed by a squaramide has been realized. The method affords a series of 2-CF3-2-indole-substituted thiochromanes featuring a CF3-containing quaternary stereocenter in excellent yields, diastereoselectivities, and enantioselectivities.