高度对映选择性的烯酮与手性环状 2-酰胺二烯的 Diels-Alder 环加成反应，其中 2-酰胺二烯来源于烯丙酰胺。
A highly stereoselective Diels-Alder cycloaddition of enones with chiral cyclic 2-amidodienes derived from allenamides.
机构信息
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53705, United States.
出版信息
Org Lett. 2013 Sep 20;15(18):4842-5. doi: 10.1021/ol402254p. Epub 2013 Sep 3.
Abstract
Lewis acid promoted Diels-Alder cycloadditions of a series of de novo chiral cyclic 2-amidodienes are described. These cyclic 2-amidodienes are derived from chiral α-allyl allenamides via a sequence of E-selective 1,3-H shift and 6π-electron pericyclic ring closure. With enones serving as effective dienophiles, these cycloadditions can be highly diastereoselective depending upon the chiral amide substituent, thereby representing a facile entry to optically enriched [2.2.2]bicyclic manifolds.
摘要
本文描述了一系列新型手性环状 2-酰胺二烯在路易斯酸促进下的 Diels-Alder 环加成反应。这些环状 2-酰胺二烯是通过 E-选择性的 1,3-H 迁移和 6π 电子周环闭环反应，从手性 α-烯丙基烯胺酰胺衍生而来的。当烯酮作为有效的亲二烯体时，这些环加成反应具有高度的非对映选择性，这取决于手性酰胺取代基，因此代表了一种容易获得手性 [2.2.2]双环骨架的方法。
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