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.


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