Related Experiment Video
Updated: Aug 16, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Enolate addition to a 2-alkylidene[1,3]dithiane-derived bissulfoxide. A new a(2)-acceptor
Tobias Wedel1, Joachim Podlech
1Institut für Organische Chemie, Universität Karlsruhe (TH), Karlsruhe 76131, Germany.
Abstract:
Reaction of enolates derived from esters and ketones to an easily prepared alkylidene[1,3]dithiane-1,3-dioxide afforded the respective adducts with good yields and selectivities generally exceeding 85:15. The base used for enolate addition played no significant role for the reaction outcome, and addition of a silyl enole ether gave similar results. The thus formed oxygenated S,S-acetals were transformed into the corresponding 1,4-dicarbonyls by a reduction/oxidation sequence with 84% yield. [reaction: see text]
More Related Videos
06:46Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Reactivity of Enolate Ions
Preparation and Reactions of Sulfides
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene