One-pot synthesis of chiral multifunctionalized aziridines

被引：15

作者：

Fioravanti, Stefania ^{[1
]}

Morea, Sara ^{[1
]}

Morreale, Alberto ^{[1
]}

Pellacani, Lucio ^{[1
]}

Tardella, Paolo A. ^{[1
]}

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy

来源：

TETRAHEDRON | 2009年 / 65卷 / 02期

关键词：

Michael addition; Amination; Asymmetric induction; Heterocycles; DIASTEREOSELECTIVE CYCLOPROPANATION; KNOEVENAGEL CONDENSATION; ASYMMETRIC-SYNTHESIS; HOMOCHIRAL KETALS; DIMETHYLZINC;

D O I：

10.1016/j.tet.2008.11.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct synthetic procedure to obtain chiral aziridines is reported, involving a diastereoselective aza-MIRC (Michael Initiated Ring Closure) reaction. Multifunctionalized aziridines are obtained in high overall yields (82-92%) and with a diastereomeric ratio up to 99:1. Further synthetic elaboration can lead to the formation of interesting biochemical molecules, such as amino glycosides. The diastereomeric induction seems to be strongly controlled both by the choice of chiral moiety and by the electron withdrawing groups (EWG) present on the starting alkenes. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：484 / 488

页数：5

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