Kinetic resolution of 2H-azirinesviaCu(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides

被引：12
|
作者：
Deng, Hua [1 ,2 ]
Liu, Tian-Tian [1 ,2 ]
Ding, Zheng-Dong [1 ,2 ]
Yang, Wu-Lin [1 ,2 ]
Luo, Xiaoyan [1 ,2 ]
Deng, Wei-Ping [1 ,2 ,3 ]
机构：
[1] East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China
[3] Zhejiang Normal Univ, Dept Chem, Key Lab, Minist Educ Adv Catalysis Mat, Jinhua 321004, Zhejiang, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 20期
基金：
中国国家自然科学基金;
关键词：
AZACYCLOPROPENE; 2H-AZIRINES; CHEMISTRY; ESTERS;
D O I：
10.1039/d0qo00789g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient kinetic resolution of racemic 2H-azirines has been achieved by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides. With an (S,S-p)-Ph-Phosferrox/Cu(MeCN)(4)BF(4)complex as the catalyst, optically pure 2H-azirines were obtained with excellent enantioselectivities (up to 99% ee) and high resolution efficiency (Sfactors up to 845). Meanwhile, this process provided a direct approach to synthesize structurally novel 1,3-diazabicyclo[3.1.0]hexane derivatives with excellent enantioselectivities (94-99% ee).
引用
收藏
页码：3247 / 3252
页数：6
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