Stereoselective synthesis of heterosubstituted aziridines and their functionalization

被引：30

作者：

De Vitis, L

Florio, S

Granito, C

Ronzini, L

Troisi, L

Capriati, V

Luisi, R

Pilati, T

机构：

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

[2] Univ Lecce, Dipartimento Sci & Tecnol Biol Ambientali, I-73100 Lecce, Italy

[3] CNR, Inst Chim Composti OrganoMetallici, Sez Bari, I-70126 Bari, Italy

[4] Univ Milan, CNR, Inst Mol Sci & Technol, I-20133 Milan, Italy

来源：

TETRAHEDRON | 2004年 / 60卷 / 05期

关键词：

heterosubstituted aziridines; aziridinyl anion; nucleophilic addition;

D O I：

10.1016/j.tet.2003.11.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiated (alpha-chloroalkyl)heterocycles, generated by deprotonation with LDA at -78 degreesC in THF, add to various enantiopure imines affording 'one pot' chiral heterosubstituted aziridines in a diastereoselective manner. Lithiated heterosubstituted aziridines, obtained by deprotonation of the corresponding aziridines with n-BuLi at -78 degreesC in THF, were trapped by electrophiles (D2O or CH3I) with high stereoselectivity. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：1175 / 1182

页数：8

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