A Diels-Alder approach to the stereoselective synthesis of 2,3,5,6-tetra- and 2,3,4,5,6-pentasubstituted piperidines
A Diels-Alder approach to the stereoselective synthesis of 2,3,5,6-tetra- and 2,3,4,5,6-pentasubstituted piperidines
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DOI：
10.1021/ol052436v
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发表时间：
2005-12-22
期刊：
影响因子：
5.2
通讯作者：
Charette, AB
中科院分区：
文献类型：
--
作者：
Sales, M;Charette, AB
由N-保护的2-甲基-1，2-二氢吡啶衍生的2-氮杂双环[2.2.2]辛烯Diels-Alder加合物经氧化裂解，立体选择性地合成了2，3，5，6-四取代和2，3，4，5，6-五取代哌啶。还证明了手性助剂介导的五取代哌啶的不对称合成。该方法结合了正交保护基团，从而提供了具有容易修饰的多样性点的哌啶支架。
A stereoselective synthesis of 2,3,5,6-tetra- and 2,3,4,5,6-pentasubstituted piperidines was achieved from oxidative cleavage of 2-aza-bicyclo-[2.2.2]octene Diels-Alder adducts derived from N-protected 2-methyl-1,2-dihydropyridine. A chiral auxiliary mediated asymmetric synthesis of the pentasubstituted piperidine is also demonstrated. This methodology incorporates orthogonal protecting groups, thus providing a piperidine scaffold with easily modified points of diversity.