Chiral Benzazaborole‐Catalyzed Regioselective Sulfonylation of Unprotected Carbohydrate Derivatives
- 7 August 2019
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 25 (56) , 12920-12923
Abstract
Chiral benzazaborole‐catalyzed regioselective sulfonylations of unprotected carbohydrate derivatives have been developed. This methodology enables direct regioselective functionalization of the secondary OH group in carbohydrate in the presence of the primary OH group. By using the chiral organoboron catalysis, kinetic resolution of the carbohydrate derivatives was also achieved.Keywords
Funding Information
- Japan Society for the Promotion of Science (19K15553)
This publication has 67 references indexed in Scilit:
- Catalyst recognition of cis-1,2-diols enables site-selective functionalization of complex moleculesNature Chemistry, 2013
- Enantioselective silyl protection of alcohols promoted by a combination of chiral and achiral Lewis basic catalystsNature Chemistry, 2013
- Organotin‐Catalyzed Highly Regioselective Thiocarbonylation of Nonprotected Carbohydrates and Synthesis of Deoxy Carbohydrates in a Minimum Number of StepsChemistry – A European Journal, 2012
- Functional Group Tolerance in Organocatalytic Regioselective Acylation of CarbohydratesThe Journal of Organic Chemistry, 2009
- Asymmetric Direct Amide Synthesis by Kinetic Amine Resolution: A Chiral Bifunctional Aminoboronic Acid Catalyzed Reaction between a Racemic Amine and an Achiral Carboxylic AcidAngewandte Chemie International Edition, 2008
- Asymmetric Direct Amide Synthesis by Kinetic Amine Resolution: A Chiral Bifunctional Aminoboronic Acid Catalyzed Reaction between a Racemic Amine and an Achiral Carboxylic AcidAngewandte Chemie, 2008
- Chemo- and Stereoselective Monobenzoylation of 1,2-Diols Catalyzed by Organotin CompoundsThe Journal of Organic Chemistry, 2000
- Regiospecific Glycosidation of Unprotected Sugars via Arylboronic ActivationJournal of the American Chemical Society, 1999
- Utilization of Sugars in Organic Synthesis. XXIII. Part XXII: Lithium Aluminum Hydride Reduction of Glycopyranoside-Monosulfonates: Formation of Branched Furanosides.Chemical and Pharmaceutical Bulletin, 1991
- Stereoselective total syntheses of the naturally occurring enantiomers of N-acetylneuraminic acid and 3-deoxy-D-manno-2-octulosonic acid. A new and stereospecific approach to sialo and 3-deoxy-D-manno-2-octulosonic acid conjugatesJournal of the American Chemical Society, 1988