Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2024

Borrowing hydrogen C-alkylation with secondary saturated heterocyclic alcohols

Résumé

The borrowing hydrogen methodology (BH) has emerged as a powerful tool for the rapid construction of C–C bonds, offering a greener alternative to traditional multi-step syntheses. This methodology involves the activation of inactivated alcohols followed by condensation or aldolization, ultimately leading to the regeneration of the saturated product. Herein, we report the C-alkylation of a hindered ketone with challenging secondary saturated heterocyclic alcohols. Our study encompasses the optimization of reaction conditions using either an iridium or a ruthenium catalyst and exploration of substrate scope. We demonstrate the efficient synthesis of substituted pyrrolidines and piperidines directly from a triol precursor, showcasing the versatility of this methodology. Moreover, we illustrate the post-functionalization of BH products, significantly broadening their chemical utility.

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hal-04875931 , version 1 (09-01-2025)

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Jordan François, Maïwenn Jacolot, Florence Popowycz. Borrowing hydrogen C-alkylation with secondary saturated heterocyclic alcohols. Organic & Biomolecular Chemistry, 2024, 22 (22), pp.4502-4507. ⟨10.1039/D4OB00543K⟩. ⟨hal-04875931⟩
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