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Asymmetric Pd/Organoboron‐Catalyzed Site‐Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol.
- Source :
-
Angewandte Chemie . 5/21/2024, Vol. 136 Issue 21, p1-15. 15p. - Publication Year :
- 2024
-
Abstract
- Herein, 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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *CARBOHYDRATES
*HYDROGEN bonding interactions
*TRANSITION metals
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 136
- Issue :
- 21
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 177191673
- Full Text :
- https://doi.org/10.1002/ange.202400912