Selective Hydrofunctionalization of N-Allenyl Derivatives with Heteronucleophiles Catalyzed by Brønsted Acids.
J Org Chem
; 89(4): 2320-2342, 2024 Feb 16.
Article
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| MEDLINE
| ID: mdl-38298114
ABSTRACT
In this study, we present a novel and environmentally sustainable protocol for the γ-hydrofunctionalization of N-allenyl compounds using various heteronucleophiles catalyzed solely by simple Brønsted acids. The method displays remarkable attributes, highlighting its sustainability, efficiency, regio- and stereoselectivity, as well as its versatile applicability to diverse heteroatom-containing enamides. Notably, our approach eliminates the need for metal catalysts and toxic solvents, representing a significant advancement in greener chemistry practices. We demonstrate the broad scope of our protocol by successfully scaling up reactions to gram-scale syntheses, underscoring its robustness for potential industrial implementation. The resulting γ-heterosubstituted enamides offer new possibilities for further synthetic transformations, yielding highly functionalized compounds with diverse applications. Mechanistic investigations reveal the pivotal role of CSA as a catalyst, enabling alcohol addition via a covalent activation mode.
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MEDLINE
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Guideline
Idioma:
En
Revista:
J Org Chem
Año:
2024
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Article