Ag(I)-Catalyzed Regioselective Ring-Opening of N-Tosylaziridine and N-Tosylazetidine with S-, O-, and N-Nucleophiles and Tethered Dinucleophiles

被引：43

作者：

Bera, Milan ^{[1
]}

Pratihar, Sanjay ^{[1
]}

Roy, Sujit ^{[1
,2
]}

机构：

[1] Indian Inst Technol, Dept Chem, Organometall & Catalysis Lab, Kharagpur 721302, W Bengal, India

[2] Indian Inst Technol, Sch Basic Sci, Bhubaneswar 751013, Orissa, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 05期

关键词：

EFFICIENT METHOD; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ACTIVATED AZIRIDINES; SELECTIVE ALKYLATION; ASYMMETRIC-SYNTHESIS; CHIRAL AZIRIDINES; FACILE SYNTHESIS; C-ARYLATION; IN-SITU;

D O I：

10.1021/jo102285z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[Ag(COD)(2)]PF6 catalyzes the ring-opening of N-tosylaziridines and -azetidines with alcohols, amines, thiols, and related tethered 1,2-ethane dinucleophiles. Initial rate studies and DFT-based evaluation of stepwise energetics suggest an inverse relationship between the nucleophilic reactivity of a heteroatom donor and its binding affinity to cationic Ag(I).

引用

页码：1475 / 1478

页数：4

共 76 条

[71] DABCO: An efficient organocatalyst in the ring-opening reactions of aziridines with amines or thiols [J].

Wu, J ;

Sun, XY ;

Li, YZ .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) :4271-4275

[72] A highly efficient and general method for the ring-opening of aziridines with various nucleophiles in DMSO [J].

Wu, Jie ;

Sun, Xiaoyu ;

Sun, Wei .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (22) :4231-4235

[73] LiClO4-catalyzed cleavage of aziridines with thiols:: A facile synthesis of β-aminosulfides [J].

Yadav, J. S. ;

Reddy, B. V. S. ;

Baishya, G. ;

Reddy, P. Venkatram ;

Narsaiah, A. V. .

CATALYSIS COMMUNICATIONS, 2006, 7 (10) :807-810

[74] Montmorillonite clay catalyzed cleavage of aziridines with alcohols [J].

Yadav, JS ;

Reddy, BVS ;

Balanarsaiah, E ;

Raghavendra, S .

TETRAHEDRON LETTERS, 2002, 43 (29) :5105-5107

[75] From σ- to π-electrophilic Lewis acids.: Application to selective organic transformations [J].

Yamamoto, Yoshinori .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) :7817-7831

[76]

Zwanenburg B, 2001, TOP CURR CHEM, V216, P93

← 1 2 3 4 5 6 7 8 →