反応と合成の進歩シンポジウム 発表要旨概要
第37回反応と合成の進歩シンポジウム
セッションID: 1O-05
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10:00~11:20 口頭発表 (座長 竹本 佳司)
Box-Pd(II) 錯体を用いたプロパルギルカルバメートの新規環化反応:5-アルコキシ-3(2H)-フラノン類の一段階合成法の開発
*日下部 太一高橋 健男河合 泰子高山 博之持田 智行加藤 恵介
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Furanones are well known as basic components of natural products, some of which display a wide range of characteristic physiological properties. Transition-metal catalyzed transformations of propargyl compounds have been widely used for the construction of a variety of carbo- and heterocycles. Tamaru et al. reported the cyclization of O-propargyl carbamates afforded oxazolidinones. Herein, we report a one-step synthesis of 5-alkoxy-3(2H)-furanones 2 via a novel box-Pd(II) catalyzed carbonylative cascade reaction of propargyl carbamates 1. The reaction of 1 in the presence of [PhboxPd(tfa)2] (5 mol %) and p-benzoquinone (1.5 equiv.) in methanol under CO atmosphere (balloon) afforded 2 in 56-99 % yield. The first asymmetric version of this transformation is also discussed.

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