使用钯催化剂高效生成氧化吡啶叶立德及其与几种亲偶极体的[5+2]环加成反应。
Efficient generation of an oxidopyrylium ylide using a Pd catalyst and its [5+2] cycloadditions with several dipolarophiles.
作者信息
Suga Hiroyuki, Iwai Taichi, Shimizu Masahiro, Takahashi Kie, Toda Yasunori
机构信息
Department of Materials Chemistry, Faculty of Engineering, Shinshu University, Wakasato, Nagano 380-8553, Japan.
出版信息
Chem Commun (Camb). 2018 Jan 25;54(9):1109-1112. doi: 10.1039/c7cc09552j.
PMID:29333548
Abstract
An efficient method for the generation of an oxidopyrylium ylide from 6-acetoxy-6-acetoxymethyl-2H-pyran-3(6H)-one using a Pd catalyst and [5+2] cycloadditions of the resulting ylide are described. Among substituted styrene derivatives as dipolarophiles, electron-rich styrenes showed higher yield (up to 80%). The [5+2] cycloaddition reactions can also be applied to exo-methylene cyclic compounds, and an improved method for the synthesis of polygalolide intermediate has been demonstrated.
摘要
描述了一种使用钯催化剂从6-乙酰氧基-6-乙酰氧基甲基-2H-吡喃-3(6H)-酮生成氧化吡啶叶立德的有效方法，以及所得叶立德的[5+2]环加成反应。在作为亲偶极体的取代苯乙烯衍生物中，富电子苯乙烯显示出更高的产率（高达80%）。[5+2]环加成反应也可应用于亚甲基环外化合物，并已证明了一种合成聚戊内酯中间体的改进方法。
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