Bajtos Barbora, Yu Ming, Zhao Hongda, Pagenkopf Brian L
Department of Chemistry, The University of Western Ontario, London, Ontario, N6A 1Y2, Canada.
J Am Chem Soc. 2007 Aug 8;129(31):9631-4. doi: 10.1021/ja067821+. Epub 2007 Jul 14.
The annulation reaction between various indoles and 2-alkoxycyclopropanoate esters is reported. Both high efficiency and complete stereochemical control were observed in some cases with this annulation process. A single stereocenter on the cyclopropane controls the diastereoselective formation of up to four new stereocenters. A different reaction course was observed with 3-substituted indole substrates, and an intervening C-3 to C-2-migration process arose that gives synthetically useful C-2 alkylation indole products.
报道了各种吲哚与2-烷氧基环丙烷羧酸酯之间的环化反应。在某些情况下，该环化过程具有高效率和完全的立体化学控制。环丙烷上的单个立体中心控制着多达四个新立体中心的非对映选择性形成。对于3-取代的吲哚底物，观察到了不同的反应过程，并且出现了一个中间的从C-3到C-2的迁移过程，该过程产生了具有合成用途的C-2烷基化吲哚产物。
