Ivanova Olga A, Andronov Vladimir A, Vasin Vladimir S, Shumsky Alexey N, Rybakov Victor B, Voskressensky Leonid G, Trushkov Igor V
Department of Chemistry , M. V. Lomonosov Moscow State University , Leninskie gory 1-3 , Moscow 119991 , Russian Federation.
Laboratory of Chemical Synthesis , Dmitry Rogachev National Research Center of Pediatric Hematology, Oncology, and Immunology , Samory Mashela 1 , Moscow 117997 , Russian Federation.
Org Lett. 2018 Dec 21;20(24):7947-7952. doi: 10.1021/acs.orglett.8b03491. Epub 2018 Dec 5.
Lewis-acid-induced domino transformations of donor-acceptor cyclopropanes, possessing a nucleophilic center embedded in a donor group, into functionalized 2,3-dihydrobenzo[ b]furans and 2,3-dihydrobenzo[ b]thiophenes are reported herein. An unusual switch of the electrophilic center in the three-membered ring, from the atom bearing a donor substituent to an unsubstituted carbon atom, was achieved by a judicious choice of Lewis acid, which induces the isomerization of a cyclopropane to an electrophilic alkene, and the length of linker, connecting a nucleophilic moiety and the small ring.
本文报道了路易斯酸诱导供体-受体环丙烷（其供体基团中嵌入亲核中心）转化为功能化的2,3-二氢苯并[b]呋喃和2,3-二氢苯并[b]噻吩的多米诺反应。通过明智地选择路易斯酸以及连接亲核部分和小环的连接体长度，实现了三元环中亲电中心的异常转换，即从带有供体取代基的原子转换为未取代的碳原子，其中路易斯酸可诱导环丙烷异构化为亲电烯烃。
