C-2/c-3 annulation and C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters |
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| Authors: | Bajtos Barbora Yu Ming Zhao Hongda Pagenkopf Brian L |
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| Institution: | Department of Chemistry, The University of Western Ontario, London, Ontario, N6A 1Y2, Canada. |
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| Abstract: | 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. |
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