Synthesis of optically active trifluoromethyl substituted diaziridines and oxaziridines

被引：24

作者：

Carroccia, Laura ^{[1
]}

Fioravanti, Stefania ^{[1
]}

Pellacani, Lucio ^{[1
]}

Sadun, Claudia ^{[1
]}

Tardella, Paolo A. ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2011年 / 67卷 / 30期

关键词：

Amination; Diastereoselectivity; Small heterocycles; STEREOSELECTIVE-SYNTHESIS; DIRECT AMINATION; AZIRIDINES; IMINES; REARRANGEMENTS; CHEMISTRY;

D O I：

10.1016/j.tet.2011.05.097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(E)-Trifluoromethyl imines were considered as ideal substrates to be transformed into the corresponding diaziridines by a direct amination reaction with nosyloxycarbamates. The diastereoselective induction was strongly controlled by the N-substituent Similar results were obtained in the epoxidation reactions performed on the same substrates using m-CPBA as oxidant. Starting from enantiopure imines chiral diaziridines or oxaziridines were obtained with very high enantiopurity. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5375 / 5381

页数：7

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