Asymmetric Azidation-Cycloaddition with Open-Chain Peptide-Based Catalysts. A Sequential Enantioselective Route to Triazoles
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- 作者：David J. Guerin and Scott J. Miller
- 刊名：Journal of the American Chemical Society
- 出版年：2002
- 出版时间：March 13, 2002
- 年：2002
- 卷：124
- 期：10
- 页码：2134 - 2136
- 全文大小：66K
- 年卷期：v.124,no.10(March 13, 2002)
- ISSN：1520-5126
文摘
A family of 
-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 
,-unsaturated carboxylate derivatives has been achieved, enabling application to a sequential asymmetric azidation/cycloaddition for the synthesis of optically enriched triazoles and triazolines.
-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 ,-unsaturated carboxylate derivatives has been achieved, enabling application to a sequential asymmetric azidation/cycloaddition for the synthesis of optically enriched triazoles and triazolines.