Toward a Chemical Constructor: A Lego-Like Approach for Formal α-Alkylation of Cyclic Ketones.
J Org Chem
; 89(11): 8208-8219, 2024 Jun 07.
Article
em En
| MEDLINE
| ID: mdl-38764429
ABSTRACT
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.
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MEDLINE
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En
Ano de publicação:
2024
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Article