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

doi:10.1055/s-0037-1611547

Synthesis, Table of Contents

Synthesis 2019; 51(17): 3327-3335
DOI: 10.1055/s-0037-1611547

paper

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

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Abstract

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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

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References

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