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Synlett 1999; 1999(6): 786-788
DOI: 10.1055/s-1999-2708
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cis- and trans-3-(3-Indolyl)proline Derivatives as Conformationally Restricted Analogues of Tryptophan

D. Damour* , J.-P. Pulicani, M. Vuilhorgne, S. Mignani
  • *Rhône-Poulenc Rorer SA, Centre de Recherche de Vitry-Alfortville, 13 Quai Jules Guesde-BP 14, 94403, Vitry-sur-Seine Cedex, France; Fax 33 (1) 55 71 80 63; E-mail: dominique.damour@rp-rorer.fr
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Publication Date:
31 December 1999 (online)

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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.

constrained amino acids - tryptophan analogue - 3-(3-indolyl)prolines - cycloaddition - azomethine ylide

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