Amine-Promoted Synthesis of Vinyl Aziridines

被引：30

作者：

Armstrong, Alan ^{[1
]}

Pullin, Robert D. C. ^{[1
]}

Jenner, Chloe R. ^{[1
]}

Scutt, James N. ^{[2
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] Syngenta Ltd, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

HIGHLY STEREOSELECTIVE-SYNTHESIS; (E)-ALKENE DIPEPTIDE ISOSTERES; ASYMMETRIC AZIRIDINATION; ENANTIOSELECTIVE AZIRIDINATION; MEDIATED AZIRIDINATION; ORGANOCOPPER REAGENTS; CHIRAL AZIRIDINES; N-SULFONYLIMINES; VINYLAZIRIDINES; ROUTE;

D O I：

10.1021/jo100407s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Unsubstituted vinyl aziridines were synthesized via an amine-promoted regioselective nucleophilic aziridination of alpha,beta,gamma,delta-unsaturated carbonyl compounds. The reaction is completely regioselective (> 95: 5) for the alpha,beta-alkene and completely diastereoselective, affording the trans-vinyl aziridine in moderate-to-good yields.

引用

页码：3499 / 3502

页数：4

共 51 条

[1]

Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO

[2]

2-E

[3] AZA-[2,3]-WITTIG REARRANGEMENTS OF VINYLAZIRIDINES AS A NOVEL ENTRY TO INDOLIZIDINE ALKALOIDS - ENANTIOSELECTIVE TOTAL SYNTHESIS OF INDOLIZIDINE 209D [J].

AHMAN, J ;

SOMFAI, P .

TETRAHEDRON LETTERS, 1995, 36 (02) :303-306

[4] Enantioselective aziridination reaction of α,β-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates [J].

Arai, Hiromi ;

Sugaya, Naomi ;

Sasaki, Neri ;

Makino, Kazuishi ;

Lectard, Sylvain ;

Hamada, Yasumasa .

TETRAHEDRON LETTERS, 2009, 50 (26) :3329-3332

[5] Direct synthesis of aliphatic vinyl aziridines [J].

Arini, LG ;

Sinclair, A ;

Szeto, P ;

Stockman, RA .

TETRAHEDRON LETTERS, 2004, 45 (08) :1589-1591

[6] Amine-promoted, organocatalytic aziridination of enones [J].

Armstrong, Alan ;

Baxter, Carl A. ;

Lamont, Scott G. ;

Pape, Andrew R. ;

Wincewicz, Richard .

ORGANIC LETTERS, 2007, 9 (02) :351-353

[7] N-amino-N-methylmorpholinium salts: Highly active aziridination reagents for chalcones [J].

Armstrong, Alan ;

Carbery, David R. ;

Lamont, Scott G. ;

Pape, Andrew R. ;

Wincewicz, Richard .

SYNLETT, 2006, (15) :2504-2506

[8]

ATKINSON RS, 1967, CHEM COMMUN, P1232

[9] Unprotected Vinyl Aziridines: Facile Synthesis and Cascade Transformations [J].

Baktharaman, Sivaraj ;

Afagh, Nicholas ;

Vandersteen, Adelle ;

Yudin, Andrei K. .

ORGANIC LETTERS, 2010, 12 (02) :240-243

[10] Lewis Acid Catalyzed [1,3]-Sigmatropic Rearrangement of Vinyl Aziridines [J].

Brichacek, Matthew ;

Lee, DongEun ;

Njardarson, Jon T. .

ORGANIC LETTERS, 2008, 10 (21) :5023-5026

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