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铜催化的α-(1-羟基-1-烷基和-芳基)甲基丙二烯酸酯的分子内氢烷氧基化反应,通过 5-endo 模式制备 2-烷基-和 2-芳基-2,5-二氢呋喃。

Copper-catalyzed intramolecular hydroalkoxylation of α-(1-hydroxy-1-alkyl- and -aryl)methylallenoates by a 5-endo mode for preparation of 2-alkyl- and 2-aryl-2,5-dihydrofurans.

机构信息

Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea.

出版信息

J Org Chem. 2012 Jan 6;77(1):215-20. doi: 10.1021/jo2018125. Epub 2011 Dec 1.

DOI:10.1021/jo2018125
PMID:22103563
Abstract

Ethyl α-(1-hydroxy-1-alkyl)methylallenoates and α-(1-hydroxy-1-aryl)methylallenoates containing not only electron-donating groups but also an electron-withdrawing group on the aryl group at the α-position have been shown to undergo an efficient and selective copper-catalyzed intramolecular hydroalkoxylation to give functionalized 3-ethoxycarbonyl-2-alkyl- and -aryl-2,5-dihydrofurans in good to excellent yields through a 5-endo mode.

摘要

含有不仅供电子基团而且在α-位芳基上有吸电子基团的乙基α-(1-羟基-1-烷基)甲基丙二烯酸酯和α-(1-羟基-1-芳基)甲基丙二烯酸酯,已经显示出在铜催化下能够有效地和选择性地进行分子内羟烷氧基化,通过 5-endo 模式以良好至优异的收率得到官能化的 3-乙氧羰基-2-烷基-和-芳基-2,5-二氢呋喃。

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Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters.
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