烯烃
化学
亲核细胞
胺化
试剂
臭氧分解
催化作用
药物化学
有机化学
立体化学
组合化学
作者
Zhiqi He,José María Villagrán Moreno,Manisha Swain,Jason H. Wu,Ohyun Kwon
出处
期刊:Science
[American Association for the Advancement of Science (AAAS)]
日期:2023-08-25
卷期号:381 (6660): 877-886
被引量:2
标识
DOI:10.1126/science.adi4758
摘要
Great efforts have been directed toward alkene π bond amination. In contrast, analogous functionalization of the adjacent C(sp 3 )–C(sp 2 ) σ bonds is much rarer. Here we report how ozonolysis and copper catalysis under mild reaction conditions enable alkene C(sp 3 )–C(sp 2 ) σ bond–rupturing cross-coupling reactions for the construction of new C(sp 3 )–N bonds. We have used this unconventional transformation for late-stage modification of hormones, pharmaceutical reagents, peptides, and nucleosides. Furthermore, we have coupled abundantly available terpenes and terpenoids with nitrogen nucleophiles to access artificial terpenoid alkaloids and complex chiral amines. In addition, we applied a commodity chemical, α-methylstyrene, as a methylation reagent to prepare methylated nucleosides directly from canonical nucleosides in one synthetic step. Our mechanistic investigation implicates an unusual copper ion pair cooperative process.
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