Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119991, Russia.
J Org Chem. 2011 Nov 4;76(21):8852-68. doi: 10.1021/jo201612w. Epub 2011 Oct 5.
The ability of donor-acceptor cyclopropanes to (3 + 3)-cyclodimerize is disclosed. It has been found that Lewis acid-induced transformations of 2-(hetero)arylcyclopropane-1,1-dicarboxylates containing electron-abundant aromatic substituents led to the construction of six-membered cyclic systems. Depending on the substrate properties and the Lewis acid applied, three types of products can be obtained: (1) 1,4-diarylcyclohexanes, (2) 1-aryl-1,2,3,4-tetrahydronaphthalenes, and (3) 9,10-dihydroanthracenes.
本文揭示了给体-受体环丙烷的(3+3)-环二聚化能力。研究发现,路易斯酸诱导的含富电子芳基取代基的 2-(杂)芳基环丙烷-1,1-二羧酸酯的转化导致了六元环系统的构建。根据底物性质和所用路易斯酸的不同,可以得到三种类型的产物:(1)1,4-二芳基环己烷,(2)1-芳基-1,2,3,4-四氢萘,和(3)9,10-二氢蒽。