本論文主要探討的是進行α–胺基酸的脫羰基反應後，利用格里納試劑進行碳－碳鍵的形成反應。我們的方法可以合成2號位置有官能基取代的吡咯啶及哌啶等衍生物，而合成此類化合物的關鍵是利用醯氯化試劑形成亞胺離子中間體，並使用格里納試劑作為親核性試劑進行加成反應，生成碳–碳鍵。我們使用包含sp3-, sp2- 和 sp-碳的格里納試劑進行反應，探討反應的廣泛應用性，期望此方法可應用於一些生物鹼的簡易合成。

關鍵字：脫羰基反應、碳－碳鍵形成反應、格里納試劑

This master's thesis is focus on the decarbonylative C－C bond formation of N-alkylated cyclic α-amino acids followed by the reaction with Grigard reagents. The methodology enables the synthesis of a series of 2-substituted pyrrolidine and piperidine derivatives. The key step involves the formation of iminium intermediates from the acid chloride generated in situ. And Grignard reagents were used as nucleophiles to construct C－C bond. The scope of the Grignard reactions with sp3-, sp2- and sp-carbon nucleophiles was tolerant. The versatility of the method could be used to explore the concise synthesis of bioactive alkaloids.

Key word：decarbonylative、C－C bond formation、Grignard reagents

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