Stereoselective trans- and cis-dihydroxylations of 2H-pyranyl and dihydropyridinyl heterocycles synthesized from formal [3 + 3]-cycloaddition reactions of alpha,beta-unsaturated iminium ions with 1,3-dicarbonyl equivalents.
Stereoselective trans- and cis-dihydroxylations of 2H-pyranyl and dihydropyridinyl heterocycles synthesized from formal [3 + 3]-cycloaddition reactions of alpha,beta-unsaturated iminium ions with 1,3-dicarbonyl equivalents.
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由 α,β-不饱和亚胺离子与 1,3-二羰基当量的正式 [3 3]-环加成反应合成的 2H-吡喃基和二氢吡啶基杂环的立体选择性反式和顺式二羟基化。
DOI：
10.1021/ol010034r
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发表时间：
2001
期刊：
影响因子：
5.2
通讯作者：
Zificsak,CA
中科院分区：
文献类型：
--
作者：
Zehnder,LR;Wei,LL;Hsung,RP;Cole,KP;McLaughlin,MJ;Shen,HC;Sklenicka,HM;Wang,J;Zificsak,CA
我们在这里描述了一个固有的问题，直接环氧化的内环烯烃在2h -吡喃融合成2-吡喃。这些困难导致了这些烯烃体系的高立体选择性的反式和顺式二羟基化的发展，在2h -吡喃和二氢吡啶中融合成2-吡喃或2-环己酮。还报道了去除活化的烯丙基羟基的方法。
We describe here an inherent problem in direct epoxidation of the endocyclic olefin in 2H-pyrans fused to 2-pyrones. Such difficulties led to the development of highly stereoselectivetrans-andcis-dihydroxylations of these olefinic systems in both 2H-pyrans and dihydropyridines fused to a 2-pyrones or a 2-cyclohexenone. Protocols for the removal of the activated allylic hydroxyl group are also reported.