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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 31, Pages 9631-9634Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja067821+
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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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