Catalytic Asymmetric Transformations of Racemic Aziridines

被引：31

作者：

Chai, Zhuo ^{[1
]}

机构：

[1] Anhui Normal Univ, MOE Key Lab Funct Mol Solids, Anhui Lab Mol Based Mat, Inst Organ Chem,Coll Chem & Mat Sci, 189 South Jiuhua Rd, Wuhu 241002, Anhui, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2020年 / 52卷 / 12期

基金：

中国国家自然科学基金;

关键词：

aziridine; ring opening; kinetic resolution; dynamic kinetic asymmetric transformation; asymmetric catalysis; 3+2 CYCLOADDITION; KINETIC RESOLUTION; VINYL AZIRIDINES; CONCISE SYNTHESIS; RAC-AZIRIDINES; ALKYLATION; SUBSTITUTION; REACTIVITY; ALDEHYDES; INDOLES;

D O I：

10.1055/s-0039-1690857

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic asymmetric ring-opening transformations of aziridines represent an important strategy for the construction of various chiral nitrogen-containing molecular architectures. This short review covers the progress achieved in the catalytic asymmetric transformation of racemic aziridines, focusing on the catalytic strategies employed for each different type of such aziridines.

引用

页码：1738 / 1750

页数：13

共 67 条

[1] Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition
Arena, Giada
Chen, C. Chun
Leonori, Daniele
Aggarwal, Varinder K.
[J]. ORGANIC LETTERS, 2013, 15 (16) : 4250 - 4253
[2] Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations
Bhat, Vikram
Welin, Eric R.
Guo, Xuelei
Stoltz, Brian M.
[J]. CHEMICAL REVIEWS, 2017, 117 (05) : 4528 - 4561
[3] ENANTIOSPECIFIC AND STEREOSPECIFIC RHODIUM(I)-CATALYZED CARBONYLATION AND RING EXPANSION OF AZIRIDINES - ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS AND THE KINETIC RESOLUTION OF AZIRIDINES
CALET, S
URSO, F
ALPER, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) : 931 - 934
[4] Aziridines in Formal [3+2] Cycloadditions: Synthesis of Five-Membered Heterocycles
Cardoso, Ana L.
Pinho e Melo, Teresa M. V. D.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (33) : 6479 - 6501
[5] Synthesis of Chiral Vicinal Diamines by Silver(I)-Catalyzed Enantioselective Aminolysis of N-Tosylaziridines
Chai, Zhuo
Yang, Pei-Jun
Zhang, Hu
Wang, Shaowu
Yang, Gaosheng
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (02) : 650 - 654
[6] Copper(I)-Catalyzed Kinetic Resolution of N-Sulfonylaziridines with Indoles: Efficient Construction of Pyrroloindolines
Chai, Zhuo
Zhu, You-Min
Yang, Pei-Jun
Wang, Shaoyin
Wang, Shaowu
Liu, Zhen
Yang, Gaosheng
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (32) : 10088 - 10091
[7] Cooperative Tertiary Amine/Chiral Iridium Complex Catalyzed Asymmetric [4+3] and [3+3] Annulation Reactions
Chen, Zhi-Chao
Chen, Zhi
Yang, Zhen-Hong
Guo, Li
Du, Wei
Chen, Ying-Chun
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (42) : 15021 - 15025
[8] Enantioselective Synthesis and Stereoselective Ring Opening of N-Acylaziridines
Cockrell, Jennifer
Wilhelmsen, Christopher
Rubin, Heather
Martin, Allen
Morgan, Jeremy B.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) : 9842 - 9845
[9] A Masked 1,3-Dipole Revealed from Aziridines
Dauban, Philippe
Malik, Guillaume
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) : 9026 - 9029
[10] Recent Advances in the Stereoselective Synthesis of Aziridines
Degennaro, Leonardo
Trinchera, Piera
Luisi, Renzo
[J]. CHEMICAL REVIEWS, 2014, 114 (16) : 7881 - 7929

← 1 2 3 4 5 6 7 →