Silver(<scp>i</scp>)-catalyzed stereoselective Meyer–Schuster-type rearrangement: synthesis of densely substituted α-iodo α,β-unsaturated thioesters-Reference-Cited by-同舟云学术

Silver(i)-catalyzed stereoselective Meyer–Schuster-type rearrangement: synthesis of densely substituted α-iodo α,β-unsaturated thioesters

Published:2024 Issue:3 Volume:48 Page:1164-1171
ISSN:1144-0546
Container-title:New Journal of Chemistry
language:en
Short-container-title:New J. Chem.

Author:

Lopes José L.¹^ORCID,Baldassari Lucas L.¹,Lüdtke Diogo S.¹^ORCID

Affiliation:

1. Instituto de Química, Universidade Federal do Rio Grande do Sul, UFRGS, Av. Bento Gonçalves 9500, 91501-970, Porto Alegre, RS, Brazil

Abstract

Herein, we report our approach for a Meyer–Schuster type rearrangement to access α-iodo α,β-unsaturated thioesters from propargyl thioalkynes using a silver(i) catalyst and N-iodosuccinimide as an electrophilic iodine source.

Funder

Conselho Nacional de Desenvolvimento Científico e Tecnológico

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior

Instituto Nacional de Ciência e Tecnologia de Catálise em Sistemas Moleculares e Nanoestruturados

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,General Chemistry,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2024/NJ/D3NJ05144G

Reference58 articles.

1. Metal-Free Hydropyridylation of Thioester-Activated Alkenes via Electroreductive Radical Coupling

2. Conversion mechanism of enoyl thioesters into acyl thioesters catalyzed by 2-enoyl-thioester reductases from Candida Tropicalis

3. Regioselective 1,4-Conjugate Addition of Grignard Reagents to α,β–γ,δ-Dienones and α,β–γ,δ-Dienyl Thiol Esters

4. Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates

5. Stereoselective Synthesis of 2,6-Cis-Substituted Tetrahydropyrans: Brønsted Acid-Catalyzed Intramolecular Oxa-Conjugate Cyclization of α,β-Unsaturated Ester Surrogates