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**Homo-Mannich reaction** is an extension of the classic Mannich reaction, using **high allylamines** (amines containing γ-alkene or alkynyl groups) instead of conventional aldimines, and reacting with aldehydes/ketones and nucleophilic reagents (such as phenols, indoles) to form **δ-amino carbonyl compounds** (with one more methylene unit than Mannich products).
### **Reaction Mechanism**
1. **Amide Formation**: The aldehyde/ketone reacts with the high allyamine to form an amide intermediate.
2. **Nucleophilic Addition**: The γ-position (rather than the α-position) of the alkene is attacked by the nucleophilic reagent, forming a new C-C bond (*J. Org. Chem.* **2008**, _73_, 5582).
### **Applications**
1. **Natural Product Synthesis**: Constructing the δ-amino structure of indole alkaloids (such as the aspidosperma framework) (*Org. Lett.* **2015**, _17_, 4324).
2. **Drug Molecules**: Synthesizing heterocycles with remote amino groups (such as analgesic analogues).
3. **Enantioselective Catalysis**: Obtaining optically active δ-amino acid derivatives through asymmetric catalysis (*Angew. Chem. Int. Ed.* **2019**, _58_, 10913). **Feature**: It extends the carbon chain length of the Mannich reaction and is suitable for the construction of complex structures.
