通过级联环化进行亲电芳香异戊烯基化反应。
Electrophilic aromatic prenylation via cascade cyclization.
作者信息
Kodet John G, Topczewski Joseph J, Gardner Kevyn D, Wiemer David F
机构信息
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294 USA.
出版信息
Tetrahedron. 2013 Oct 4;69(44):9212-9218. doi: 10.1016/j.tet.2013.08.056.
Abstract
To gain access to prenylated hexahydroxanthenes, tandem cascade cyclization-electrophilic aromatic substitution reactions have been studied on substrates bearing allylic and propargylic substituents. Both BF·OEt and TMSOTf can be used to initiate this reaction sequence, resulting in different ratios of the C-2 and C-6 substitution products. Even though allylic transposition is observed in some cases, the results of a crossover experiment are consistent with an intramolecular reaction sequence. Taken together, these studies now allow preparation of either the C-2 or C-6 prenylated hexahydroxanthene products.
摘要
为了获得异戊烯基化的六氢呫吨，已对带有烯丙基和炔丙基取代基的底物进行了串联级联环化-亲电芳香取代反应研究。BF·OEt和TMSOTf均可用于引发该反应序列，从而得到不同比例的C-2和C-6取代产物。尽管在某些情况下观察到了烯丙基重排，但交叉实验的结果与分子内反应序列一致。综上所述，这些研究现在使得制备C-2或C-6异戊烯基化的六氢呫吨产物成为可能。
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