cis- and trans-3-(3-indolyl)proline derivatives as conformationally restricted analogues of tryptophan
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 decarb...
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Published in | Synlett no. 6; pp. 786 - 788 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
STUTTGART
Thieme Medical Publishers
01.06.1999
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Subjects | |
Online Access | Get more information |
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Summary: | 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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ISSN: | 0936-5214 1437-2096 |
DOI: | 10.1055/s-1999-2708 |