Stereoselective aza-Diels-Alder reactions with 2H-azirines as dienophiles furnishing highly functionalized tetrahydropyridines.
Stereoselective aza-Diels-Alder reactions with 2H-azirines as dienophiles furnishing highly functionalized tetrahydropyridines.
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DOI：
10.1039/b300849e
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发表时间：
2003-04
影响因子：
4.9
通讯作者：
Åsa Sjöholm Timén;A. Fischer;P. Somfai
中科院分区：
文献类型：
--
作者：
Åsa Sjöholm Timén;A. Fischer;P. Somfai
首次实现了手性辅助衍生化 2H-氮丙啶的高度非对映选择性路易斯酸介导的氮杂-狄尔斯-阿尔德反应，生成双环和三环杂环化合物，包含氮丙啶和四氢吡啶子结构，de 高达 97%；通过X射线晶体学证实了主要产物的绝对立体化学。
Highly diastereoselective Lewis acid mediated aza-Diels-Alder reactions of chiral auxiliary derivatized 2H-azirines have been accomplished for the first time, yielding bi and tri-cyclic heterocyclic compounds, comprising aziridine and tetrahydropyridine substructures, in up to 97% de; with the absolute stereochemistry of the major product confirmed by X-ray crystallography.