Regioselective Ring-Opening Nucleophilic Addition of Aziridines through Photoredox Catalyst

被引：40

作者：

Sun, Hongnan ^{[1
]}

Yang, Chao ^{[1
]}

Lin, Run ^{[1
]}

Xia, Wujiong ^{[1
,2
]}

机构：

[1] Harbin Inst Technol, Acad Fundamental & Interdisciplinary Sci, State Key Lab Urban Water Resource & Environm, Harbin 150080, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 13期

关键词：

aziridines; photoredox catalysis; regioselective ring opening; visible light; VISIBLE-LIGHT PHOTOREDOX; C-BOND-CLEAVAGE; SILYLATED NUCLEOPHILES; N-TOSYLAZIRIDINES; MESO-AZIRIDINES; ENANTIOSELECTIVE DESYMMETRIZATION; HIGHLY EFFICIENT; FACILE SYNTHESIS; COMPLEXES; FUNCTIONALIZATION;

D O I：

10.1002/adsc.201400476

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A mild and efficient procedure was developed for the regioselective ring-opening nucleophilic addition reactions of aziridines via visible light photoredox catalysis, that provides a practical synthetic access to 1,2-bifunctional compounds. Furthermore, the regioselective synthesis of non-racemic amino ethers from chiral aziridine could also be achieved under mild conditions. Finally, a possible reaction mechanism was proposed and further supported by control experiments.

引用

页码：2775 / 2780

页数：6

共 50 条

[1] Progress towards the regioselective nucleophilic ring opening of aziridines
Whitmore, Jeremy L.
White, Olivia
Hart, Matthew E.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
[2] A practical regioselective ring-opening of activated aziridines with organoalanes
Bertolini, Ferruccio
Woodward, Simon
Crotti, Stefano
Pineschi, Mauro
[J]. TETRAHEDRON LETTERS, 2009, 50 (31) : 4515 - 4518
[3] REGIOSELECTIVE NUCLEOPHILIC RING-OPENING OF OXABICYCLIC COMPOUNDS
LAUTENS, M
CHIU, P
[J]. TETRAHEDRON LETTERS, 1993, 34 (05) : 773 - 776
[4] Regioselective ring-opening of aziridines with thiophenol in the presence of β-cyclodextrin in water
Reddy, MS
Narender, M
Rao, KR
[J]. SYNLETT, 2005, (03) : 489 - 490
[5] Synthesis of (+)-Lycoricidine by the Application of Oxidative and Regioselective Ring-Opening of Aziridines
Yadav, J. S.
Satheesh, G.
Murthy, Changalvala V. S. R.
[J]. ORGANIC LETTERS, 2010, 12 (11) : 2544 - 2547
[6] Nucleophilic ring opening of aziridines
Hu, XE
[J]. TETRAHEDRON, 2004, 60 (12) : 2701 - 2743
[7] Nucleophilic ring opening of aziridines
Stamm, H
[J]. JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1999, 341 (04): : 319 - 331
[8] Regioselective ring-opening of aziridines with potassium thiocyanate in the presence of β-cyclodextrin in water
Reddy, MS
Narender, M
Nageswar, YVD
Rao, KR
[J]. TETRAHEDRON LETTERS, 2005, 46 (38) : 6437 - 6439
[9] A Mild and Regioselective Ring-Opening of Aziridines with Acid Anhydride Using TBD or PS-TBD as a Catalyst
Matsukawa, Satoru
Mouri, Yasutaka
[J]. MOLECULES, 2015, 20 (10): : 18482 - 18495
[10] Regioselective ring-opening of aziridines with potassium thiocyanate and thiols using sulfated zirconia as a heterogeneous recyclable catalyst
Das, B
Ramu, R
Ravikanth, B
Reddy, KR
[J]. TETRAHEDRON LETTERS, 2006, 47 (05) : 779 - 782

← 1 2 3 4 5 →