cis- and trans-3-(3-Indolyl)proline Derivatives as Conformationally Restricted Analogues of Tryptophan

Abstract
A method for the diastereoselective generation of 3-indolyl-3-proline derivatives has been developed. The [3+2] cycloaddition reaction of 3-vinylindoles with dimethyl N-ethoxycarbonyl-N-methoxymethylaminomalonate in the presence of TiCl4, afforded the title compounds after acid hydrolysis and decarboxylation reactions. These new amino acids may be viewed as conformationally restricted mimetics of tryptophan.

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