Toward a Chemical Constructor: A Lego-Like Approach for Formal α-Alkylation of Cyclic Ketones

Autor: Frolov, Andriy I., Chuchvera, Yaroslav O., Ostapchuk, Eugeniy N., Druzhenko, Tetiana V., Volochnyuk, Dmytro M., Ryabukhin, Serhiy V.
Zdroj: The Journal of Organic Chemistry; 20240101, Issue: Preprints
Abstrakt: A conceptual strategy for a formal α-alkylation of α-methylene ketones was developed. Diverse 1° and 2° alkyl substituents were generated in the α-position of various ketones via synthesis of enaminone (step 1) and treatment with organomagnesium (step 2) with subsequent catalytic hydrogenation (step 3, 1° alkyl) or organocopper reagents (step 4, 2° alkyl). Tolerance toward ester, Boc-protected amine, and α-fluoro-substituted ketone moieties was demonstrated. The suitability of the method for late-stage natural product modification was shown.
Databáze: Supplemental Index