Efficient ring opening reactions of N-tosyl aziridines with amines and water in presence of catalytic amount of cerium(IV) ammonium nitrate

被引：25

作者：

Chakraborty, TK ^{[1
]}

Ghosh, A ^{[1
]}

Raju, TV ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

CHEMISTRY LETTERS | 2003年 / 32卷 / 01期

关键词：

D O I：

10.1246/cl.2003.82

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

While methyl- and benzylamines opened N-tosyl aziridines 1 very efficiently in acetonitrile with complete regio- and stereo-selectivity to give the corresponding diamines 2 and 3, respectively, in excellent yields, similar openings with water could only be achieved in the presence of a catalytic amount of cerium(IV) ammonium nitrate under very mild conditions furnishing the amino alcohols 4.

引用

页码：82 / 83

页数：2

共 40 条

[1] RING-OPENING OF N-TOSYL AZIRIDINES BY 2-LITHIODITHIANES
HOWSON, W
OSBORN, HMI
SWEENEY, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (19): : 2439 - 2445
[2] RING-OPENING OF N-TOSYL AZIRIDINES BY SULFUR-STABILIZED NUCLEOPHILES
OSBORN, HMI
SWEENEY, JB
HOWSON, B
[J]. SYNLETT, 1993, (09) : 675 - 676
[3] The organocatalytic ring-opening polymerization of N-tosyl aziridines by an N-heterocyclic carbene
Bakkali-Hassani, Camille
Rieger, Elisabeth
Vignolle, Joan
Wurm, Frederik R.
Carlotti, Stephane
Taton, Daniel
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (62) : 9719 - 9722
[4] N-heterocyclic olefins catalyzed ring-opening polymerization of N-tosyl aziridines
Zhou, Li
Wang, Zhenyu
Xu, Guangqiang
Yang, Rulin
Yan, Huating
Hao, Xin-Qi
Wang, Qinggang
[J]. EUROPEAN POLYMER JOURNAL, 2020, 140
[5] Catalyst-Free Regio- and Stereospecific Synthesis of β-Sulfonamido Dithiocarbamates: Efficient Ring-Opening Reactions of N-Tosyl Aziridines by Dialkyldithiocarbamates
Alagiri, Kaliyamoorthy
Prabhu, Kandikere Ramaiah
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) : 6922 - 6925
[6] Ceric ammonium nitrate (CAN) catalyzed ring cleavage of N-tosyl aziridines:: a potential tool for solution phase library generation
Chandrasekhar, S
Narsihmulu, C
Sultana, SS
[J]. TETRAHEDRON LETTERS, 2002, 43 (41) : 7361 - 7363
[7] Nickel/Photo-Cocatalyzed Regioselective Ring Opening of N-Tosyl Styrenyl Aziridines with Aldehydes
Fan, Pei
Jin, Youxiang
Liu, Jiawei
Wang, Rui
Wang, Chuan
[J]. ORGANIC LETTERS, 2021, 23 (19) : 7364 - 7369
[8] Ring-opening of N-Tosyl Aziridines with Hydroxyl Compounds Catalyzed by Acidic Ionic Liquid
Li Yuling
Gu Dagong
Xu Xiaoping
Ji Shunjun
[J]. CHINESE JOURNAL OF CHEMISTRY, 2009, 27 (08) : 1558 - 1562
[9] Selective and efficient oxidation of sulfides to sulfoxides using ammonium cerium (IV) nitrate in the presence of a catalytic amount of KBr or NaBr
Zolfigol, Mohammad Ali
Amani, Kamal
Hajjami, Maryam
Ghorbani-Choghamarani, Arash
[J]. MONATSHEFTE FUR CHEMIE, 2008, 139 (08): : 895 - 899
[10] Selective and efficient oxidation of sulfides to sulfoxides using ammonium cerium (IV) nitrate in the presence of a catalytic amount of KBr or NaBr
Mohammad Ali Zolfigol
Kamal Amani
Maryam Hajjami
Arash Ghorbani-Choghamarani
[J]. Monatshefte für Chemie - Chemical Monthly, 2008, 139

← 1 2 3 4 →