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

Author:

Guo Hao12,Kirchhoff Jan‐Lukas3ORCID,Strohmann Carsten3ORCID,Grabe Bastian4ORCID,Loh Charles C. J.12ORCID

Affiliation:

1. Abteilung Chemische Biologie Max Planck Institut für Molekulare Physiologie Otto-Hahn-Straße 11 44227 Dortmund Germany

2. Fakultät für Chemie und Chemische Biologie Technische Universität Dortmund Otto-Hahn-Straße 4a 44227 Dortmund Germany

3. Technische Universität Dortmund Fakultät für Chemie und Chemische Biologie Anorganische Chemie Otto-Hahn-Straße 6 44227 Dortmund Germany

4. NMR Department Fakultät für Chemie und Chemische Biologie Technische Universität Dortmund Otto-Hahn-Straße 4a 44227 Dortmund Germany

Abstract

AbstractHerein, we demonstrate the robustness of a synergistic chiral Pd/organoboron system in tackling a challenging suite of site‐, regio‐, enantio‐ and diastereoselectivity issues across a considerable palette of biologically relevant carbohydrate polyols, when prochiral alkoxyallenes were employed as electrophiles. In view of the burgeoning role of noncovalent interactions (NCIs) in stereoselective carbohydrate synthesis, our mechanistic experiments and DFT modeling of the reaction path unexpectedly revealed that NCIs such as hydrogen bonding and CH‐π interactions between the resting states of the Pd‐π‐allyl complex and the borinate saccharide are critically involved in the stereoselectivity control. Our strategy thus illuminates the untapped potential of harnessing NCIs in the context of transition metal catalysis to tackle stereoselectivity challenges in carbohydrate functionalization.

Funder

Boehringer Ingelheim Stiftung

Fonds der Chemischen Industrie

Konrad-Adenauer-Stiftung

Deutsche Forschungsgemeinschaft

Publisher

Wiley

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