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Synthesis of β-Alkylated Enamides by Copper-Catalyzed Anti-Stereoselective and β-Regioselective 1,2-Alkylamination of Alkynes
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K
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J
DOI：10.1002/adsc.70262.png)
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Abstract
En 中文
Polysubstituted alkenes are versatile molecules and their multidimensional transformations have significant promotion for the creation and screening of chemotherapeutic agents and polyolefin functional materials. The difunctionalization of alkynes is an inevitable pathway for the generation of highly substituted alkenes with specific conformations. However, there is currently limited development on the construction of β-alkylated enamides through 1,2-alkylamination of alkynes, and the newly generated CC and CN bonds in traditional reports maintain syn-stereoselectivity. In addition, the formation of anti CC/CN bonds through difunctionalization of alkynes via free radical processes is overly dependent on electron deficient fluorinated alkyl radicals. We therefore seek to explore anti-stereoselective and β-regioselective 1,2-alkylamination of alkynes with amides and azobis(alkylcarbonitriles). Dozens of all-new β-alkylated enamides, including those containing biologically active patterns, are exported in 38%–88% yields by combining the addition of alkyl radicals to CC triple bonds with copper chelate-assisted functionalization of vinyl radicals. In addition, extensive mechanism explorations and synthetic applications are also conducted to explore the details and potential of this protocol.
Keywords:
alkylamination
alkynes
azobis(alkylcarbonitriles)
copper
polysubstituted alkenes
Journal
A
IF:
4
Papers:
1.0W
Citations:
2.6W
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Cited Papers