Synthesis of alkylidenephthalans through fluoride-induced cyclization of electron-deficient 2-siloxymethylphenylacetylene derivatives
Synthesis of alkylidenephthalans through fluoride-induced cyclization of electron-deficient 2-siloxymethylphenylacetylene derivatives
复制标题
DOI：
10.1016/j.tet.2007.01.046
复制
发表时间：
2007-04-02
期刊：
影响因子：
2.1
通讯作者：
Herndon, James W.
中科院分区：
文献类型：
--
作者：
Duan, Shaofeng;Cress, Karen;Herndon, James W.
以羰基取代的炔为特征的甲硅烷基化的2-炔基苄醇衍生物的基于氟的脱保护导致直接合成亚烷基邻苯二甲酸乙烯基酯。该反应是选择性的Z亚烷基酞在一个化学控制的过程。类似的化合物也产生于Fischer卡宾络合物与2-炔基苯甲酰基衍生物在水性溶剂体系中的偶联中。随后的酸催化的分子间或分子内Diels-Alder反应导致氢化萘或氢化菲衍生物。(c)2007爱思唯尔有限公司保留所有权利。
Fluoride-based deprotection of silylated 2-alkynylbenzyl alcohol derivatives featuring carbonyl-substituted alkynes results in the direct synthesis of alkylidenephthalan vinylogous esters. The reaction is selective for the Z alkylidenephthalans in a thermodynamically controlled process. Similar compounds are also produced in the coupling of Fischer carbene complexes with 2-alkynylbenzoyl derivatives in an aqueous solvent system. Subsequent acid-catalyzed inter- or intramolecular Diels-Alder reactions lead to hydronaphthalene or hydrophenanthrene derivatives. (c) 2007 Elsevier Ltd. All rights reserved.