Stereoselective synthesis of sulfonated 1-indenones via radical-triggered multi-component cyclization of β-alkynyl
Zheng-Jia Shen1, Ya-Nan Wu, Chun-Lan He
1School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, 221116, P. R. China. jiangchem@jsnu.edu.cn laotu@jsnu.edu.cn.
Abstract:
New radical-triggered multi-component cyclizations of β-alkynyl propenones have been developed, leading to 50 examples of sulfonated 1-indenones with generally good yields and high levels of stereoselectivity. The oxidant-free azosulfonylation of β-alkynyl propenones with aryldiazonium salts and DABSO was realized under the neutral-redox conditions where TBHP enabled the direct selenosulfonylation of β-alkynyl propenones by combining sulfinic acids and diphenyl diselenide. This protocol features a broad substrate scope, high functional group tolerance and mild reaction conditions.
More Related Videos
05:34Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
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
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Preparation and Reactions of Sulfides
