Amine-Catalyzed Three-Component Cascade Reaction between Alcohols or Thiols, Activated Alkenes, and Enones: A Simple and Chemoselective Synthesis of Densely Functionalized Compounds

Haiyun Sun; Bo Zhang; Xiangyu Chen; Zhengjie He

doi:10.1055/s-0036-1588716

Synthesis, Table of Contents

Synthesis 2017; 49(10): 2205-2214
DOI: 10.1055/s-0036-1588716

paper

Amine-Catalyzed Three-Component Cascade Reaction between Alcohols or Thiols, Activated Alkenes, and Enones: A Simple and Chemoselective Synthesis of Densely Functionalized Compounds

Haiyun Sun

^aThe State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China Email: zhengjiehe@nankai.edu.cn

,

Bo Zhang

^aThe State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China Email: zhengjiehe@nankai.edu.cn

,

Xiangyu Chen

^aThe State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China Email: zhengjiehe@nankai.edu.cn

,

Zhengjie He*

^aThe State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China Email: zhengjiehe@nankai.edu.cn

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China

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Abstract

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Abstract

A highly chemoselective three-component cascade reaction among alcohols or thiols, electron-deficient alkenes, and α,β-unsaturated ketones takes place under the catalysis of triethylamine, providing densely functionalized chain products in 44–99% yields. The transformation presumably proceeds through a sequential cascade of hetero-Michael/Michael reactions.

Key words

multicomponent reactions - hetero-Michael addition - alcohols - thiols - alkenes - enones

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References

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