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
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
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通过二溴氟甲基卡宾酯的铬介导转化制备 (Z)-1-氟-1-链烯基羧酸酯、碳酸酯和氨基甲酸酯以及作为双酰基供体的反应性
DOI：
10.1016/j.jfluchem.2011.07.022
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发表时间：
2012
影响因子：
1.9
通讯作者：
Hikaru Yanai
中科院分区：
文献类型：
--
作者：
下田康嗣;小谷俊介;杉浦正晴;中島 誠;Hikaru Yanai
CrCl_2/Mn介导的各种二溴氟甲基甲酸酯（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迁移重排生成1-氟-1-烯基酯。在温和的条件下（室温下，在THF中），用CrCl_2/Mn体系进行反应，以良好的收率和优异的Z选择性得到1-氟-1-烯基酯。由此获得的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充当双酰基供体。
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 ester thus obtained acts as a double acyl donor in the reaction with necleophiles such as amine, thiol, alcohol as well as bifunctional necleophiles such as ethylene diamine derivative.