Synthesis 2017; 49(10): 2205-2214
DOI: 10.1055/s-0036-1588716
paper
© Georg Thieme Verlag Stuttgart · New York

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
a   The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: zhengjiehe@nankai.edu.cn
,
Bo Zhang
a   The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: zhengjiehe@nankai.edu.cn
,
Xiangyu Chen
a   The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: zhengjiehe@nankai.edu.cn
,
Zhengjie He*
a   The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: zhengjiehe@nankai.edu.cn
b   Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 24 December 2016

Accepted after revision: 23 January 2017

Publication Date:
21 February 2017 (online)


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.

Supporting Information