Enantiomerically pure 2-aryl(alkyl)-2-trifluoromethylaziridines: synthesis and ring opening with selected O- and N-nucleophiles

被引：27

作者：

Grellepois, Fabienne ^{[1
]}

Nonnenmacher, Jean ^{[1
]}

Lachaud, Fabien ^{[1
]}

Portella, Charles ^{[1
]}

机构：

[1] Univ Reims, Inst Chim Mol Reims, UMR CNRS 6229, UFR Sci Exactes & Nat, F-51687 Reims 2, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 04期

关键词：

ALPHA-TRIFLUOROMETHYL; STEREOSELECTIVE-SYNTHESIS; AZIRIDINES; CHEMISTRY; ALCOHOLS; CARBON;

D O I：

10.1039/c0ob00690d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein the synthesis of enantiomerically pure 2-phenyl- and 2-ethyl-2-trifluoromethylaziridines by Mitsunobu-type cyclisation of the corresponding N-protected amino alcohols, and our results regarding their ring opening with selected nucleophiles. Under basic conditions, N-tosyl aziridines have been regioselectively opened at the less hindered carbon. Under acidic conditions, the regioselectivity of the attack depends on the nature of the substituent at C-2 and on the nitrogen protecting group.

引用

页码：1160 / 1168

页数：9

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