2-(Acetoxymethyl)buta-2,3-dienoate, a versatile 1,4-biselectrophile for phosphine-catalyzed (4 + n) annulations with 1,n-Bisnucleophiles (n = 1, 2)

Journal of the American Chemical Society
Qiongmei ZhangXiaofeng Tong

Abstract

A novel PPh(3)-catalyzed (4 + n) annulation of 2-(acetoxymethyl)buta-2,3-dienoates 1c-e with 1,n-bisnucleophiles (n = 1, 2) has been developed to provide a facile synthetic method for cyclopentene and 1,2,3,6-tetrahydropyridazine derivatives. The acetate group of 2-(acetoxymethyl)buta-2,3-dienoate is crucial for the formation of 1,4-biselectrophilic intermediate C, which is recognized to be a 1,4-biselectrophile that can react with 1,n-bisnucleophiles. Deuterium studies also suggest that the reaction pathway involves a proton-transfer process.

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Citations

Sep 21, 2010·Chemical Communications : Chem Comm·Chaolong LiXiaofeng Tong
Jun 17, 2016·Accounts of Chemical Research·Tianli WangYixin Lu
Jun 17, 2016·Journal of the American Chemical Society·Chunjie Ni, Xiaofeng Tong
May 14, 2014·Chemistry, an Asian Journal·Yin Wei, Min Shi
Sep 24, 2015·Chemical Communications : Chem Comm·Vasudeva Rao Gandi, Yixin Lu
May 18, 2018·Chemistry : a European Journal·Sébastien ClergueRaphaël Robiette
Jan 25, 2012·Angewandte Chemie·Shichao Yu, Shengming Ma
Jan 6, 2011·Chemistry : a European Journal·Fernando López, José Luis Mascareñas
Aug 4, 2015·Chemistry : a European Journal·Olivier RousseauRaphaël Robiette
Mar 30, 2019·Organic & Biomolecular Chemistry·Kostiantyn O Marichev, Michael P Doyle
Aug 7, 2019·Chemical Communications : Chem Comm·Zhenjie GanZheng Duan
Dec 19, 2019·Chemical Communications : Chem Comm·Er-Qing Li, You Huang
Apr 26, 2012·Advanced Synthesis & Catalysis·Chengfeng JingHongchao Guo

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