Asymmetric azidation-cycloaddition with open-chain peptide-based catalysts. A sequential enantioselective route to triazoles
Asymmetric azidation-cycloaddition with open-chain peptide-based catalysts. A sequential enantioselective route to triazoles
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DOI：
10.1021/ja0177814
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发表时间：
2002-03-13
影响因子：
15
通讯作者：
Miller, SJ
中科院分区：
文献类型：
--
作者：
Guerin, DJ;Miller, SJ
合成了一类含β-取代组氨酸的多肽，以研究非共价构象硬化对催化剂对映选择性的影响。在叠氮化合物与α，β-不饱和羧酸衍生物的共轭加成反应中，实现了对映选择性的无敌意增强，使其能够应用于顺序的不对称叠氮/环加成反应来合成光学富集的三唑和三唑啉。
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.