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

被引：4

作者：

Zheng, Xiaojun ^{[1
]}

Deng, Qifu ^{[1
]}

Hou, Qinglin ^{[1
]}

Zhang, Kaiqiang ^{[1
]}

Wen, Pushan ^{[1
]}

Hu, Shunqin ^{[1
]}

Wang, Haifei ^{[1
]}

机构：

[1] Hunan Univ Technol, Coll Life Sci & Chem, Zhuzhou 412007, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 12期

关键词：

secondary amine; amidophosphanes; silver carbonate; 1; 3-dipolar cycloaddition; pyrrolidines; AZOMETHINE YLIDES; COOPERATIVE CATALYSIS; CALCIUM COMPLEXES; IMINO ESTERS; ACID; DIPOLAROPHILES; PYRROLIDINES; DERIVATIVES; PYRROLIZIDINES; CONSTRUCTION;

D O I：

10.1055/s-0037-1609492

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A class of multifunctional amidophosphanes derived from chiral 1,2-diphenylethylenediamines and natural -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 ,-unsaturated aldehyde derived imino esters with different electron-deficient alkenes, as well as the three-component reaction of -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).

引用

页码：2347 / 2358

页数：12

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