Vaishanv Narendra Kumar, Gupta Ashis Kumar, Kant Ruchir, Mohanan Kishor
Academy of Scientific and Innovative Research , New Delhi 110001 , India.
J Org Chem. 2018 Aug 3;83(15):8759-8767. doi: 10.1021/acs.joc.8b01074. Epub 2018 Jun 27.
An efficient and expedient fluoride-mediated α-selective 1,6-conjugate addition of allenic esters to para-quinone methides has been developed. The reaction exhibited an excellent substrate scope, and a wide range of α-diarylmethylated allenic esters were obtained in good to excellent yields. It was further shown that the strategy could be extended to isatin-derived quinone methides yielding allenic esters containing 3,3-disubstituted oxindoles. The tert-butyl ester of α-diarylmethylated allenoate was effectively converted into γ-butenolide through a Au/Ag catalyzed cyclization strategy.
已开发出一种高效便捷的氟化物介导的丙二烯酸酯与对醌甲基化物的α-选择性1,6-共轭加成反应。该反应具有出色的底物范围，能以良好至优异的产率得到多种α-二芳基甲基化丙二烯酸酯。进一步表明，该策略可扩展至异吲哚酮衍生的醌甲基化物，得到含3,3-二取代氧化吲哚的丙二烯酸酯。通过金/银催化的环化策略，α-二芳基甲基化丙二烯酸酯的叔丁酯可有效转化为γ-丁内酯。
