Iodine(III)-Mediated Enantioselective Oxidative Contraction of Dihydropyranones
Tommy Lussier1, Claude Y Legault1
1Centre in Green Chemistry and Catalysis, Department of Chemistry, University of Sherbrooke, 2500 boul. de l'Université, Sherbrooke, Québec J1K 2R1, Canada.
Abstract:
The γ-butyrolactone motif is promising in pharmaceuticals and natural products with various biological activities. The oxidative contraction of dihydropyranones mediated by hypervalent iodine (HVI) reagents is an efficient approach of preparing this motif. We show that, using readily available chiral HVI reagents, numerous enantioenriched γ-butyrolactones are accessible. The method provides generally high enantioselectivities and modest to high yields. The resulting chiral iodoarene is easily recovered and reused for the reaction multiple times, without loss of yield or enantioselectivities.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
