Asymmetric Pd/Organoboron-Catalyzed Site-Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol

Guo H, Kirchhoff JL, Strohmann C, Grabe B, Loh CCJ. (2024) Angew Chem Int Ed Engl.


The Loh group reported lately in Angewandte Chemie the robustness of a synergistic chiral Pd/organoboron system in surmounting a challenging blend of site-, regio-, enantio- and diastereoselectivity issues in the site-selective functionalization of minimally protected saccharides with prochiral alkoxyallenes.

Through meticulous mechanistic investigations and DFT modelling, a suite of hydrogen bonding and CH-π interactions was determined to be critical in the stereoselectivity determining step. This study hence illuminates the untapped potential of harnessing noncovalent interactions in the context of asymmetric transition metal catalysis to address stereoselectivity challenges in difficult carbohydrate functionalizations.

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