Asymmetric Pd/Organoboron‐Catalyzed Site‐Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol
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.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
Asymmetric Pd/Organoboron‐Catalyzed Site‐Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol ; day:17 ; month:04 ; year:2024 ; extent:16
Angewandte Chemie ; (17.04.2024) (gesamt 16)
- Urheber
- DOI
-
10.1002/ange.202400912
- URN
-
urn:nbn:de:101:1-2404171429501.747834213312
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
14.08.2025, 10:54 MESZ
Datenpartner
Dieses Objekt wird bereitgestellt von:
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Guo, Hao
- Kirchhoff, Jan‐Lukas
- Strohmann, Carsten
- Grabe, Bastian Martin
- Loh, Charles C. J.
Ähnliche Objekte (12)
Asymmetric Pd/Organoboron‐Catalyzed Site‐Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol
Enantioconvergent and Site‐Selective Etherification of Carbohydrate Polyols through Chiral Copper Radical Catalysis
Enantioconvergent and Site‐Selective Etherification of Carbohydrate Polyols through Chiral Copper Radical Catalysis
New insights into the prevention of ureteral stents encrustation
Electrophotocatalytic hydrogenation of imines and reductive functionalization of aryl halides
Deconstruction of tropospheric chemical reactivity using aircraft measurements: the ATom data
Deconstruction of tropospheric chemical reactivity using aircraft measurements: the Atmospheric Tomography Mission (ATom) data
Heteroleptic Fe(II)-Hexa-NHC complex with 130 ps MLCT lifetime & Mechanism study of photocatalyzed synthesis of medium sized ring compounds
Highly Stretchable Micro/Nano Wrinkle Structures for Infrared Stealth Application
Shear Viscosity of Uniform Fermi Gases with Population Imbalance
Optimization of preparation conditions for Salsola laricifolia protoplasts using response surface methodology and artificial neural network modeling
Red cell distribution width/albumin ratio as a marker for metabolic syndrome: findings from a cross-sectional study
Asymmetric Pd/Organoboron‐Catalyzed Site‐Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol
Enantioconvergent and Site‐Selective Etherification of Carbohydrate Polyols through Chiral Copper Radical Catalysis
Enantioconvergent and Site‐Selective Etherification of Carbohydrate Polyols through Chiral Copper Radical Catalysis
New insights into the prevention of ureteral stents encrustation
Electrophotocatalytic hydrogenation of imines and reductive functionalization of aryl halides
Deconstruction of tropospheric chemical reactivity using aircraft measurements: the ATom data
Deconstruction of tropospheric chemical reactivity using aircraft measurements: the Atmospheric Tomography Mission (ATom) data
Heteroleptic Fe(II)-Hexa-NHC complex with 130 ps MLCT lifetime & Mechanism study of photocatalyzed synthesis of medium sized ring compounds
Highly Stretchable Micro/Nano Wrinkle Structures for Infrared Stealth Application
Shear Viscosity of Uniform Fermi Gases with Population Imbalance
Optimization of preparation conditions for Salsola laricifolia protoplasts using response surface methodology and artificial neural network modeling
Red cell distribution width/albumin ratio as a marker for metabolic syndrome: findings from a cross-sectional study
Asymmetric Pd/Organoboron‐Catalyzed Site‐Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol
Enantioconvergent and Site‐Selective Etherification of Carbohydrate Polyols through Chiral Copper Radical Catalysis
Enantioconvergent and Site‐Selective Etherification of Carbohydrate Polyols through Chiral Copper Radical Catalysis
New insights into the prevention of ureteral stents encrustation
Electrophotocatalytic hydrogenation of imines and reductive functionalization of aryl halides
Deconstruction of tropospheric chemical reactivity using aircraft measurements: the ATom data
Deconstruction of tropospheric chemical reactivity using aircraft measurements: the Atmospheric Tomography Mission (ATom) data
Heteroleptic Fe(II)-Hexa-NHC complex with 130 ps MLCT lifetime & Mechanism study of photocatalyzed synthesis of medium sized ring compounds
Highly Stretchable Micro/Nano Wrinkle Structures for Infrared Stealth Application
Shear Viscosity of Uniform Fermi Gases with Population Imbalance
Optimization of preparation conditions for Salsola laricifolia protoplasts using response surface methodology and artificial neural network modeling