Lithiation-electrophilic trapping of N-sulfonyl-activated ethylene aziridines

被引：10

作者：

Huang, Jianhui ^{[1
]}

Moore, Stephen P. ^{[1
]}

O'Brien, Peter ^{[1
]}

Whitwood, Adrian C. ^{[1
]}

Gilday, John ^{[2
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

[2] AstraZeneca, Proc R&D, Avlon Works, Bristol BS10 7ZE, Avon, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

BETA-ALKOXY AZIRIDINES; ORGANOLITHIUM-MEDIATED CONVERSION; ALLYLIC SULFONAMIDES; TERMINAL AZIRIDINES; AMINO-ALCOHOLS; REARRANGEMENT; EPOXIDES; BUTYLLITHIUM; REAGENTS; UTILITY;

D O I：

10.1039/b815957b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A detailed study on the lithiation-electrophilic trapping of N-sulfonyl ethylene aziridines is described. The optimum results required use of a N-2,4,6-tri-iso-propylbenzenesulfonyl activating group and lithiation using 3 equiv. of s-BuLi-PMDETA for 1 minute before addition of the electrophile. In situ trapping with Me3SiCl was also successful. Electrophilic trapping with aldehydes provided a stereoselective route to syn-hydroxy aziridines. Alternatively, keto aziridines could be stereoselectively reduced to syn-hydroxy aziridines using NaBH4-CeCl3. The relative stereochemistry in two of the hydroxy aziridines was established unequivocally by X-ray crystallography.

引用

页码：335 / 345

页数：11

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