A Chiral Secondary Amine–Amidophosphane Precatalyst for Silver-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions

Xiaojun Zheng; Qifu Deng; Qinglin Hou; Kaiqiang Zhang; Pushan Wen; Shunqin Hu; Haifei Wang

doi:10.1055/s-0037-1609492

Synthesis, Table of Contents

Synthesis 2018; 50(12): 2347-2358
DOI: 10.1055/s-0037-1609492

paper

A Chiral Secondary Amine–Amidophosphane Precatalyst for Silver-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions

Xiaojun Zheng

College of Life Science and Chemistry, Hunan University of Technology, Zhuzhou 412007, P. R. of China Email: wanghaifei@hut.edu.cn

,

Qifu Deng

College of Life Science and Chemistry, Hunan University of Technology, Zhuzhou 412007, P. R. of China Email: wanghaifei@hut.edu.cn

,

Qinglin Hou

College of Life Science and Chemistry, Hunan University of Technology, Zhuzhou 412007, P. R. of China Email: wanghaifei@hut.edu.cn

,

Kaiqiang Zhang

College of Life Science and Chemistry, Hunan University of Technology, Zhuzhou 412007, P. R. of China Email: wanghaifei@hut.edu.cn

,

Pushan Wen

College of Life Science and Chemistry, Hunan University of Technology, Zhuzhou 412007, P. R. of China Email: wanghaifei@hut.edu.cn

,

Shunqin Hu

College of Life Science and Chemistry, Hunan University of Technology, Zhuzhou 412007, P. R. of China Email: wanghaifei@hut.edu.cn

,

Haifei Wang*

College of Life Science and Chemistry, Hunan University of Technology, Zhuzhou 412007, P. R. of China Email: wanghaifei@hut.edu.cn

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Abstract

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◊ These authors contributed equally to this work.

Abstract

A class of multifunctional amidophosphanes derived from chiral 1,2-diphenylethylenediamines and natural α-amino acids has been developed. Among these, in combination with silver(I) salts, a chiral secondary amine–amidophosphane precatalyst has been demonstrated as being a highly efficient multifunctional precatalyst in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides, including a series of heterocyclic, aliphatic, and 2-substituted azomethine ylides, and aromatic α,β-unsaturated aldehyde derived imino esters with different electron-deficient alkenes, as well as the three-component reaction of α-imino esters generated in situ by using N,N′-diisopropylcarbodiimide as dehydrating agent. Under optimal conditions, highly functionalized endo-adducts were obtained in high to excellent yields (up to 99% yield) and enantioselectivities (up to >99.9% ee).

Key words

secondary amine - amidophosphanes - silver carbonate - 1,3-dipolar cycloaddition - pyrrolidines

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References

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Supplementary Material

Supporting Information