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Synthesis 2019; 51(17): 3327-3335
DOI: 10.1055/s-0037-1611547
paper
© Georg Thieme Verlag Stuttgart · New York

The Catalytic Asymmetric Construction of Trifluoromethylated Quaternary Carbon-Containing Thiochromans

Hui Chen
,
Cui Wang
,
Dongwa Wen
,
Yabo Deng
,
Xin Liu
,
Xueting Liu
,
Jiang Zhang*
,
Wenjin Yan*
The Institute of Pharmacology, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, P. R. of China   Email: zhangjian@lzu.edu.cn   Email: yanwj@lzu.edu.cn
› Author AffiliationsWe are grateful for the grant from the National Natural Science Foundation of China (No. 81872723).
Further Information

Publication History

Received: 27 March 2019

Accepted after revision: 24 April 2019

Publication Date:
15 May 2019 (online)

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Abstract

Trifluoromethylated chiral quaternary stereogenic carbon center at 2-position of thiochromans has been constructed through organocatalyzed Michael-aldol reaction. With quinine squaramide as catalyst, the reaction of 2-mercaptobenzaldehyde with β-aryl-β-CF3 enones or β-alkyl-β-CF3 enones gave 2-CF3-thiochromans bearing three contiguous stereogenic centers in good to excellent diastereoselectivities, enantioselectivities, and yields.

Key words

cascade reaction - asymmetric catalysis - orgnocatalytic - CF3-containing - sulfur-containing heterocycle

Supporting Information

 

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