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.