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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Bibliographic Details
Published inSynlett no. 6; pp. 786 - 788
Main Authors Damour, D, Pulicani, JP, Vuilhorgne, M, Mignani, S
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.06.1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
3-SUBSTITUTED PROLINES
tryptophan analogue
cycloaddition
azomethine ylide
3-AMINO-4-INDOLYL-2-PIPERIDONES
constrained amino acids
CONSTRAINED AMINO-ACIDS
3-(3-indolyl)prolines
STEREOSELECTIVE SYNTHESIS
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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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-1999-2708