Kinetic Resolution of trans-2,3-Aziridinyl Alcohols via Hydroxyl Directed Regio- and Enantioselective Ring Opening Reactions

被引：18

作者：

Chang, Zhe-Ran ^{[1
,2
]}

Du, Si-Si ^{[1
,2
]}

Zhang, Cui ^{[1
,2
]}

Chen, Shuang-Hu ^{[1
,2
]}

Hua, Yuan-Zhao ^{[1
,2
]}

Wang, Min-Can ^{[1
,2
]}

Mei, Guang-Jian ^{[1
,2
]}

Jia, Shi-Kun ^{[1
,2
]}

机构：

[1] Zhengzhou Univ, Coll Chem, Zhengzhou 450000, Henan, Peoples R China

[2] Zhengzhou Univ, Inst Green Catalysis, Zhengzhou 450000, Henan, Peoples R China

来源：

ACS CATALYSIS | 2023年 / 13卷 / 10期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

aziridines; dinuclear zinc catalyst; ring opening reaction; kinetic resolution; vicinal diamines; MESO-AZIRIDINES; CATALYZED DESYMMETRIZATION; AMINOLYSIS; ALKYLATION; DEAROMATIZATION; REACTIVITY; EPOXIDES; DIAMINES; INDOLES;

D O I：

10.1021/acscatal.3c01252

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An efficient kinetic resolution of racemic trans-2,3-aziridinyl alcohols is established via zinc catalyzed ring opening reactions with various amines as the nucleophiles. The directing effect of the hydroxyl group and the precise enantiodiscrimination by dinuclear zinc cooperative catalyst are the keys to success of high regioselectivity and enantioselectivity. A range of enantioenriched vicinal diamines and trans-2,3-aziridinyl alcohols were obtained in good yields with excellent ee values. To the best of our knowledge, this is the first example of directed enantioselective nucleophilic ring opening reactions of 2,3-aziridinyl alcohols.

引用

页码：6873 / 6878

页数：6

共 55 条

[1] The development of scalemic multidentate niobium complexes as catalysts for the highly stereoselective ring opening of meso-epoxides and meso-aziridines [J].