Preparation of (Z)-1-fluoro-1-alkenyl carboxylates, carbonates and carbamates through chromium mediated transformation of dibromofluoromethylcarbinyl esters and the reactivity as double acyl group donors
作者:Akio Saito、Manabu Tojo、Hikaru Yanai、Fukiko Wada、Muga Nakagawa、Midori Okada、Azusa Sato、Rieko Okatani、Takeo Taguchi
DOI:10.1016/j.jfluchem.2011.07.022
日期:2012.1
CrCl2/Mn-mediated transformation of various dibromofluoromethylcarbinyl esters including carboxylates, carbonates and carbamates provided 1-fluoro-1-alkenyl esters via [2,3]-sigmatropic rearrangement of ester group. Reaction proceeded by using CrCl2/Mn system under mild conditions (in THF at room temperature) to give 1-fluoro-1-alkenyl esters in good yield with an excellent Z selective manner. 1-Fluoro-1-alkenyl
CrCl 2 / Mn介导的各种二溴氟甲基羰基酯(包括羧酸酯,碳酸酯和氨基甲酸酯)的转化通过酯基的[2,3]-σ重排提供了1-氟-1-烯基酯。通过在温和的条件下(在室温下于THF中)使用CrCl 2 / Mn体系进行反应,以良好的收率和优异的Z选择性方式得到1-氟-1-烯基酯。如此获得的1-氟-1-烯基酯在与亲核试剂如胺,硫醇,醇以及双官能亲核试剂如乙二胺衍生物的反应中用作双酰基供体。