Related Experiment Video
Updated: Sep 25, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Copper-Catalyzed Asymmetric Oxidative Desymmetrization of 2-Substituted 1,2,3-Triols
Kosuke Yamamoto1, Yu Suganomata1, Takumi Inoue1
1Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
Abstract:
Asymmetric oxidative desymmetrization of 2-substituted glycerols has been achieved by using a new chiral bisoxazoline ligand/copper catalyst system with 1,3-dibromo-5,5-dimethylhydantoin and MeOH. The present transformation smoothly proceeds with readily accessible 2-(hetero)aryl- and alkyl-substituted glycerols and provides straightforward access toward various glycerate derivatives in good to high yields with high enantioselectivities. The synthetic utility of the present protocol was demonstrated by the transformation of the optically active glycerol into a glyceraldehyde derivative.
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

