Double axially chiral bisphosphorylimides as novel Bronsted acids in asymmetric three-component Mannich reaction

被引：58

作者：

Chen, Ying-Ying ^{[2
]}

Jiang, Yi-Jun ^{[2
]}

Fan, Yan-Sen ^{[2
]}

Sha, Di ^{[2
]}

Wang, Qifeng ^{[2
]}

Zhang, Guangliang ^{[2
]}

Zheng, Liangyu ^{[1
]}

Zhang, Suoqin ^{[2
]}

机构：

[1] Jilin Univ, Minist Educ, Key Lab Mol Enzymol & Engn, Changchun 130012, Peoples R China

[2] Jilin Univ, Coll Chem, Changchun 130012, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 11-12期

基金：

中国国家自然科学基金;

关键词：

CATALYTIC ENANTIOSELECTIVE ADDITION; EFFICIENT SYNTHESIS; ANTI-MANNICH; SYN-ALDOL; ALDEHYDES; KETONES; IMINES; MOTIF;

D O I：

10.1016/j.tetasy.2012.06.008

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A double axially chiral bisphosphorylimide has been demonstrated to be an efficient and highly sterically hindered Bronsted acid in asymmetric three-component Mannich reactions. Optically active syn-beta-amino ketones were obtained in high yields (up to 99%) with excellent diastereoselectivity (99:1) and enantioselectivity (up to 99% ee). A gram-scale reaction was also performed to prove the synthetic application value of this reaction. (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：904 / 909

页数：6

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