Synthesis and lithiation of oxazolinylaziridines:: the N-substituent effect

被引：37

作者：

Luisi, R

Capriati, V

Florio, S

Di Cunto, P

Musio, B

机构：

[1] Univ Bari, Dipartimento Farmacochim, I-70126 Bari, Italy

[2] CNR, ICCOM, Sez Bari, I-70126 Bari, Italy

来源：

TETRAHEDRON | 2005年 / 61卷 / 13期

关键词：

aziridinyllithiums; oxazolinylaziridines; aziridino-gamma-lactones; lithiation;

D O I：

10.1016/j.tet.2005.01.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of N-substituted oxazolinylaziridines and their deprotonation to afford the corresponding aziridinyllithiums is described. The chemical and configurational stability of the lithiated species depends on the N-substituent on the aziridine ring. The trapping with carbonyl compounds of (R*,S*) configurated oxazolinylaziridines is an interesting route for the preparation of functionalised alpha,beta-aziridino-gamma-lactones. (c) 2005 Elsevier Ltd. All rights reserved.

引用

收藏

页码：3251 / 3260

页数：10

相关论文

共 34 条

[1] Highly diastereoselective aziridination of imines with trimethylsilyldiazomethane.: Subsequent silyl substitution with electrophiles, ring opening, and metalation of C-silylaziridines -: A cornucopia of highly selective transformations [J].

Aggarwal, VK ;

Alonso, E ;

Ferrara, M ;

Spey, SE .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2335-2344

[2]

Alezra V, 2001, EUR J ORG CHEM, V2001, P2589

[3] Nitrogen atom transfer to alkenes utilizing chloramine-T as a nitrogen source [J].

Ando, T ;

Minakata, S ;

Ryu, I ;

Komatsu, M .

TETRAHEDRON LETTERS, 1998, 39 (3-4) :309-312

[4]

BARTNIK R, 1979, POL J CHEM, V53, P537

[5] Dual reaction pathways in the magnesium-mediated synthesis of aziridines from benzal halides and imines [J].

Biscoe, MR ;

Fry, AJ .

TETRAHEDRON LETTERS, 2001, 42 (15) :2759-2762

[6] Sugar-derived aziridines: functionalization via lithiation of the aziridine ring [J].

Bisseret, P ;

Bouix-Peter, C ;

Jacques, O ;

Henriot, S ;

Eustache, J .

ORGANIC LETTERS, 1999, 1 (08) :1181-1182

[7] [ALPHA-(DIMETHYLAMINO)BENZYLLITHIUM DIETHYL ETHER]2, (S)-ALPHA-(METHYLPIVALOYLAMINO)BENZYLLITHIUM-(-)-SPARTEINE, AND [3-IODO-2-LITHIO-1-METHYLINDOLE-2 TETRAHYDROFURAN]2 - CRYSTAL-STRUCTURE INVESTIGATIONS OF ALPHA-LITHIATED AMINES [J].

BOCHE, G ;

MARSCH, M ;

HARBACH, J ;

HARMS, K ;

LEDIG, B ;

SCHUBERT, F ;

LOHRENZ, JCW ;

AHLBRECHT, H .

CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (08) :1887-1894

[8] CYCLIZATION OF DEPROTONATED 2-PHENYL-1-TOSYLAZIRIDINE - A SURPRISING EXAMPLE OF AN INTRAMOLECULAR NUCLEOPHILIC AROMATIC ADDITION [J].

BRETERNITZ, HJ ;

SCHAUMANN, E ;

ADIWIDJAJA, G .

TETRAHEDRON LETTERS, 1991, 32 (10) :1299-1302

[9]

Capriati V, 2001, SYNTHESIS-STUTTGART, P2299

[10] Aziridination of alpha,beta-unsaturated esters by (ethoxycarbonyl)nitrene [J].

Carducci, M ;

Fioravanti, S ;

Loreto, MA ;

Pellacani, L ;

Tardella, PA .

TETRAHEDRON LETTERS, 1996, 37 (21) :3777-3778

← 1 2 3 4 →