Asymmetric Azidation−Cycloaddition with Open-Chain Peptide-Based Catalysts. A Sequential Enantioselective Route to Triazoles

A family of β-substituted histidine-containing peptides has been synthesized to probe the effect of noncovalent conformational rigidification on catalyst enantioselectivity. Unambiguous enhancement of enantioselectivity in the conjugate addition of azide to α,β-unsaturated carboxylate derivatives ha...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-03, Vol.124 (10), p.2134-2136
Main Authors: Guerin, David J, Miller, Scott J
Format: Article
Language:English
Subjects:
Catalysis
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Peptides - chemistry
Protein Structure, Secondary
Reactivity and mechanisms
Triazoles - chemical synthesis
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Summary:A family of β-substituted histidine-containing peptides has been synthesized to probe the effect of noncovalent conformational rigidification on catalyst enantioselectivity. Unambiguous enhancement of enantioselectivity in the conjugate addition of azide to α,β-unsaturated carboxylate derivatives has been achieved, enabling application to a sequential asymmetric azidation/cycloaddition for the synthesis of optically enriched triazoles and triazolines.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0177814