通过串联铑（II）催化的双环丙烷化/科普重排/狄尔斯-阿尔德反应合成复杂的六环化合物。
Synthesis of complex hexacyclic compounds via a tandem Rh(II)-catalyzed double-cyclopropanation/Cope rearrangement/Diels-Alder reaction.
作者信息
Spangler Jillian E, Lian Yajing, Raikar Sandeep N, Davies Huw M L
机构信息
Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
出版信息
Org Lett. 2014 Sep 19;16(18):4794-7. doi: 10.1021/ol502257d. Epub 2014 Sep 10.
Treatment of (E)-1-(methoxymethylene)-1,2,3,4-tetrahydronaphthalene with styryl diazoacetates in the presence of catalytic amounts of the dirhodium complex Rh2(S-DOSP)4 provides a highly enantioenriched hexacyclic product with 10 new stereogenic centers. The transformation proceeds by a cascade sequence starting with a double cyclopropanation of a benzene ring, followed by a Cope rearrangement of a divinylcyclopropane and then an intramolecular Diels-Alder cycloaddition.
在催化量的双铑配合物Rh2(S-DOSP)4存在下，用苯乙烯基重氮乙酸酯处理(E)-1-(甲氧基亚甲基)-1,2,3,4-四氢萘，可得到具有10个新立体中心的高度对映体富集的六环产物。该转化过程通过一系列串联反应进行，首先是苯环的双环丙烷化反应，接着是二乙烯基环丙烷的科普重排反应，然后是分子内狄尔斯-阿尔德环加成反应。
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