1-烷氧基-1-氨基-1,3-丁二烯的狄尔斯-阿尔德反应：6-取代和6,6-二取代的2-环己烯酮以及6-取代的5,6-二氢吡喃-2-酮的直接合成
Diels-Alder Reactions of 1-Alkoxy-1-amino-1,3-butadienes: Direct Synthesis of 6-Substituted and 6,6-Disubstituted 2-Cyclohexenones and 6-Substituted 5,6-Dihydropyran-2-ones.
作者信息
Elkin Pavel K, Durfee Nathaniel D, Rawal Viresh H
机构信息
Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.
出版信息
Org Lett. 2021 Jul 16;23(14):5288-5293. doi: 10.1021/acs.orglett.1c01031. Epub 2021 Jun 1.
Abstract
We report the cycloaddition reactions of 1-alkoxy-1-amino-1,3-butadienes. These doubly activated dienes are prepared on a multigram scale from crotonic acid chloride and its derivatives. The dienes undergo Diels-Alder (DA) and hetero-Diels-Alder (HDA) reactions under mild reaction conditions with a variety of electron-deficient dienophiles to afford cycloadducts in good yields with excellent regioselectivities. The hydrolysis of the DA cycloadducts provides 6-substituted and 6,6-disubstituted 2-cylohexenones, which are versatile building blocks for complex molecule synthesis. The corresponding HDA cycloadducts afford 6-substituted 5,6-dihydropyran-2-ones.
摘要
我们报道了1-烷氧基-1-氨基-1,3-丁二烯的环加成反应。这些双活化二烯是由巴豆酰氯及其衍生物以多克规模制备的。这些二烯在温和的反应条件下与多种缺电子亲双烯体发生狄尔斯-阿尔德（DA）反应和杂狄尔斯-阿尔德（HDA）反应，以良好的产率和优异的区域选择性得到环加合物。DA环加合物的水解提供了6-取代和6,6-二取代的2-环己烯酮，它们是复杂分子合成的通用构建块。相应的HDA环加合物得到6-取代的5,6-二氢吡喃-2-酮。
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