Exploring F/CF<sub>3</sub>substituted oxocarbenium ions for the diastereoselective assembly of highly substituted tetrahydrofurans-Reference-Cited by-同舟云学术

Exploring F/CF₃substituted oxocarbenium ions for the diastereoselective assembly of highly substituted tetrahydrofurans

Published:2023 Issue:27 Volume:59 Page:4083-4086
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Fernandes Anthony J.¹^ORCID,Michelet Bastien²^ORCID,Panossian Armen¹^ORCID,Martin-Mingot Agnès²^ORCID,Leroux Frédéric R.¹^ORCID,Thibaudeau Sébastien²^ORCID

Affiliation:

1. Université de Strasbourg, Université de Haute-Alsace, CNRS, UMR 7042-LIMA, ECPM, 25 Rue Becquerel, Strasbourg 67087, France

2. Université de Poitiers, CNRS, IC2MP, UMR 7285, Equipe “Synthèse Organique”, 4 Rue Michel Brunet, Poitiers Cedex 9 86073, France

Abstract

We report on the dramatic effect of a local partial charge inversion by replacing a CHCH3group by a CFCF3. This strategy allows the diastereoselective reduction of 5-membered ring oxocarbenium ions to access highly substituted tetrahydrofurans.

Funder

Fondation Pour la Recherche en Chimie

Université de Strasbourg

Université de Poitiers

Centre National de la Recherche Scientifique

European Regional Development Fund

Conseil Régional Aquitaine

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2023/CC/D2CC06521E

Reference46 articles.

1. Recent Advances in the Chemical Synthesis of C-Glycosides

2. Tetrahydrofuran-Containing Macrolides: A Fascinating Gift from the Deep Sea

3. An update on bioactive plant lignans

4. New 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignans from the aril of Myristica fragrans.

5. Total Synthesis of (±)-Jiadifenin, a Non-peptidyl Neurotrophic Modulator