Synthesis of enantiopure substituted aziridines by diastereoselective N-bromocyclization and nucleophile-mediated regioselective opening

被引：9

作者：

Agami, C ^{[1
]}

Amiot, F ^{[1
]}

Couty, F ^{[1
]}

Dechoux, L ^{[1
]}

机构：

[1] Univ Pierre & Marie Curie, CNRS, Lab Synth Symetr, F-75005 Paris, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(98)01109-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure beta-substituted aziridines were prepared from (S)-phenylglycinol through a key N-bromocyclization of an unsaturated iminoether. A total control of the regioselectivity was observed during the opening of these aziridines by various nucleophiles (N-3(-), H2O, EtOH, Me2CuLi). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5373 / 5374

页数：2

共 6 条

[1]

Fort S, 1997, SYNLETT, P1235

[2]

KASAI M, 1992, SYNLETT, P778

[3] Norephedrine-derived oxazolidines as chiral auxiliaries-stereocontrolled routes to R or S beta-hydroxy phosphine oxides [J].

OBrien, P ;

Warren, S .

TETRAHEDRON LETTERS, 1996, 37 (17) :3051-3054

[4] The asymmetric synthesis of aziridines [J].

Osborn, HMI ;

Sweeney, J .

TETRAHEDRON-ASYMMETRY, 1997, 8 (11) :1693-1715

[5] New chiral acetate imide enolate for stereoselective aldol reactions [J].

Palomo, C ;

Oiarbide, M ;

Gonzalez, A ;

Garcia, JM ;

Berree, F ;

Linden, A .

TETRAHEDRON LETTERS, 1996, 37 (38) :6931-6934

[6]

TANNER D, 1994, ANGEW CHEM INT EDIT, V33, P599, DOI 10.1002/anie.199405991

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