Synthesis of linear and cyclic homo-β-peptides based on a binaphthylic β-amino acid with only axial chirality

The terminally protected, linear, homo-β-peptides Boc-[(R)-β2,2-HBin]n-OMe (n=2–6) as well as the cyclic homo-β-peptides c[(R)-β2,2-HBin]3 and c[(S)-β2,2-HBin]4, all derived from the 2′,1′:1,2;1″,2″:3,4-dinaphthcyclohepta-1,3-diene-6-aminomethyl-6-carboxylic acid residue β2,2-HBin possessing only ax...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2006-01, Vol.17 (1), p.30-39
Main Authors: Gaucher, Anne, Dutot, Laurence, Barbeau, Olivier, Wakselman, Michel, Mazaleyrat, Jean-Paul, Peggion, Cristina, Oancea, Simona, Formaggio, Fernando, Crisma, Marco, Toniolo, Claudio
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary:The terminally protected, linear, homo-β-peptides Boc-[(R)-β2,2-HBin]n-OMe (n=2–6) as well as the cyclic homo-β-peptides c[(R)-β2,2-HBin]3 and c[(S)-β2,2-HBin]4, all derived from the 2′,1′:1,2;1″,2″:3,4-dinaphthcyclohepta-1,3-diene-6-aminomethyl-6-carboxylic acid residue β2,2-HBin possessing only axial chirality, have been synthesized in solution by the EDC/AtOH coupling method for chain elongation, and by cyclization of pentafluorophenyl esters. A conformational analysis suggested the concomitant occurrence of different intramolecularly H-bonded forms for the linear oligomers in solution.
ISSN:0957-4166
1362-511X
0957-4166
DOI:10.1016/j.tetasy.2005.11.021