Organocatalytic Aziridine Synthesis Using F+ Salts

被引：30

作者：

Bew, Sean P. ^{[1
]}

Fairhurst, Shirley A. ^{[2
]}

Hughes, David L. ^{[1
]}

Legentil, Laurent ^{[1
]}

Liddle, John ^{[3
]}

Pesce, Paolo ^{[1
]}

Nigudkar, Sanket ^{[1
]}

Wilson, Martin A. ^{[1
]}

机构：

[1] Univ E Anglia, Sch Chem, Norwich NR4 7TJ, Norfolk, England

[2] John Innes Ctr, Dept Biol Chem, Norwich NR4 7UH, Norfolk, England

[3] GlaxoSmithKline Res & Dev Ltd, Dept Med Chem, Med Res Ctr, Stevenage, Herts, England

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 20期

基金：

英国工程与自然科学研究理事会;

关键词：

CATALYTIC ASYMMETRIC AZIRIDINATION; FLUORINATING AGENTS; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; ESTERS; IMINES; DERIVATIVES; AMINATION;

D O I：

10.1021/ol901784m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes a unique application of the fluoronium cation (F+) as an organocatalyst for mediating the reaction between N-substituted imines and ethyl diazoacetate affording excellent yields of N-substituted aziridines.

引用

页码：4552 / 4555

页数：4

共 49 条

[11]

BEW SP, 2009, ADV SYN CAT UNPUB

[12] Short and efficient synthesis of optically active N-tosyl aziridines from 2-amino alcohols [J].

Bieber, LW ;

de Araújo, MCF .

MOLECULES, 2002, 7 (12) :902-906

[13] Asymmetric aziridine synthesis via aza-Darzens reaction of bromoacylcamphorsultam [J].

Cantrill, AA ;

Hall, LD ;

Jarvis, AN ;

Osborn, HMI ;

Raphy, J ;

Sweeney, JB .

CHEMICAL COMMUNICATIONS, 1996, (23) :2631-2632

[14] Lewis acid-catalyzed synthesis of aziridines [J].

Casarrubios, L ;

Perez, JA ;

Brookhart, M ;

Templeton, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8358-8359

[15] Application of the evans aziridination procedure to 2-substituted acrylates and cinnamates:: An expedient route to α-substituted α- and β-amino acids [J].

Dauban, P ;

Dodd, RH .

TETRAHEDRON LETTERS, 1998, 39 (32) :5739-5742

[16] Stereoselective synthesis of heterosubstituted aziridines and their functionalization [J].

De Vitis, L ;

Florio, S ;

Granito, C ;

Ronzini, L ;

Troisi, L ;

Capriati, V ;

Luisi, R ;

Pilati, T .

TETRAHEDRON, 2004, 60 (05) :1175-1182

[17] Asymmetric synthesis of aziridines by reduction of N-tert-butanesulfinyl α-chloro imines [J].

Denolf, Bram ;

Leemans, Erika ;

De Kimpe, Norbert .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (09) :3211-3217

[18] Origin of the deactivation in styrene aziridination by aryl azides, catalyzed by ruthenium porphyrin complexes.: Structural characterization of a Δ2-1,2,3-triazoline RuII(TPP)CO complex [J].

Fantauzzi, S ;

Gallo, E ;

Caselli, A ;

Ragaini, F ;

Macchi, P ;

Casati, N ;

Cenini, S .

ORGANOMETALLICS, 2005, 24 (20) :4710-4713

[19] Cobalt-catalyzed aziridination with diphenylphosphoryl azide (DPPA):: Direct synthesis of N-phosphorus-substituted aziridines from alkenes [J].

Gao, Guang-Yao ;

Jones, Jess E. ;

Vyas, Renu ;

Harden, Jeremiah D. ;

Zhang, X. Peter .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6655-6658

[20]

GREENE TW, 1991, PROTECTIVE GROUPS OR, P377

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