Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Journal of the American Chemical Society
Xing-Zhong ShuWeiping Tang

Abstract

A new type of rhodium-catalyzed [5 + 2] cycloaddition was developed for the synthesis of seven-membered rings with diverse functionalities. The ring formation was accompanied by a 1,2-acyloxy migration event. The five- and two-carbon components of the cycloaddition are 3-acyloxy-1,4-enynes (ACEs) and alkynes, respectively. Cationic rhodium(I) catalysts worked most efficiently for the intramolecular cycloaddition, while only neutral rhodium(I) complexes could facilitate the intermolecular reaction. In both cases, electron-poor phosphite or phosphine ligands often improved the efficiency of the cycloadditions. The scope of ACEs and alkynes was investigated in both the intra- and intermolecular reactions. The resulting seven-membered-ring products have three double bonds that could be selectively functionalized.

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Citations

Nov 17, 2012·Chemical Reviews·Kai E O Ylijoki, Jeffrey M Stryker
Feb 26, 2013·Chemical Communications : Chem Comm·Casi M SchienebeckWeiping Tang
May 25, 2013·Journal of the American Chemical Society·Renhe LiuWeiping Tang
Oct 19, 2016·Journal of the American Chemical Society·Scott A ShulerDonald A Watson
Jun 17, 2016·Angewandte Chemie·Minqiang Jia, Shengming Ma
Apr 4, 2018·Organic & Biomolecular Chemistry·Yong-Sheng ZhengJi-Kai Liu
Sep 7, 2017·Organic & Biomolecular Chemistry·Wangze SongWeiping Tang
Apr 29, 2016·Chemistry : a European Journal·Zhunzhun YuJunliang Zhang
Feb 6, 2015·Chemistry : a European Journal·Jin-Ming YangMin Shi
Jun 4, 2014·Angewandte Chemie·Yasuaki KawaguchiChisato Mukai
Oct 21, 2015·Angewandte Chemie·Xiaoxun LiWeiping Tang
May 26, 2021·Organic & Biomolecular Chemistry·Chunmao DongHaibo Tan
May 3, 2014·The Journal of Organic Chemistry·Andivelu Ilangovan, Gandhesiri Satish
Oct 30, 2013·Journal of the American Chemical Society·Xiaoxun LiWeiping Tang
Dec 11, 2019·Accounts of Chemical Research·Stephanie A BlaszczykWeiping Tang

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