铜催化酰腙的炔基化反应：一种构建功能化阿扎迪肽的简便方法。
Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides.
机构信息
Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.
出版信息
Org Lett. 2022 Sep 16;24(36):6614-6618. doi: 10.1021/acs.orglett.2c02625. Epub 2022 Sep 6.
We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Nonsymmetrical ynehydrazides could be obtained in 25-97% yield using azaglycine derivatives as nucleophiles. The transformation is compatible with most functional groups naturally occurring on amino acid side chains and allows the transfer of silyl-, alkyl-, and aryl-substituted alkynes. The obtained α-alkynyl azaglycine products could be further functionalized by nucleophilic attack or cycloaddition on the triple bond.
我们报告了使用乙炔基苯并[d]噁唑酮（EBX）试剂的氮杂二肽的铜催化炔基化反应。使用氮杂甘氨酸衍生物作为亲核试剂，可以以 25-97%的产率得到非对称的炔酰肼。该转化与氨基酸侧链上天然存在的大多数官能团相容，并允许硅基、烷基和芳基取代的炔烃的转移。得到的α-炔基氮杂甘氨酸产物可以通过三键上的亲核进攻或环加成进一步官能化。
Zotero 插件