Citation: Sun Haiyun, Li Yuan, Liu Wei, Zheng Yang, He Zhengjie. Organocatalytic asymmetric cascade cyclization reaction of o-hydroxy cinnamaldehydes with diphenylphosphine oxide[J]. Chinese Chemical Letters, ;2018, 29(11): 1625-1628. doi: 10.1016/j.cclet.2018.01.026 shu

Organocatalytic asymmetric cascade cyclization reaction of o-hydroxy cinnamaldehydes with diphenylphosphine oxide

Sun Haiyun ^a ,
Li Yuan ^a ,
Liu Wei ^a ,
Zheng Yang ^a ,
He Zhengjie ^a,b,,

a.
The State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
b.
Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300071, China

Corresponding author: He Zhengjie, zhengjiehe@nankai.edu.cn
Received Date: 6 December 2017
Revised Date: 4 January 2018
Accepted Date: 15 January 2018
Available Online: 1 December 2018

Figures(4)

A highly stereoselective asymmetric cascade cyclization reaction between o-hydroxycinnamaldehydes and diphenylphosphine oxide has been achieved with 84%-99% ee and 7:1-20:1 dr under the catalysis of L-diarylprolinol silyl ether. This reaction provides a facile access to highly enantioenriched 4-diphenylphosphinyl chroman-2-ols. It also represents a novel organocatalytic asymmetric phosphaMichael addition of α, β-unsaturated aldehydes with pentavalent P-nucleophiles.
- Organocatalysis,
- Asymmetric catalysis,
- Cyclization reaction,
- Phospha-Michael addition,
- Cascade reaction
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