Chemistry Publications
Document Type
Article
Publication Date
8-8-2007
Journal
Journal of the American Chemical Society
Volume
129
Issue
31
First Page
9631
Last Page
9634
URL with Digital Object Identifier
10.1021/ja067821+
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.
