Work

Charge Relocation Enables a Modular and Diastereoselective Synthesis of cis ‐Substituted Tetrahydrofurans

Year: 2025

Type: article

Abstract: Diastereoselective construction of organic scaffolds from simple and commercial materials is a powerful strategy in contemporary organic synthesis. Herein, we report a novel disconnection for the direct preparation of tetrahydrofurans (THFs) and corresponding derivatives from acyl chlorides and alkenes using charge relocation. Newly synthesised Hantzsch ester derivatives, functioning both as hydride sources and selectivity modulators, enabled exceptional diastereoselectivity. The wide range of alkenes tolerated is a highlight of the method, enabling the construction of structurally distinct THF-containing skeletons.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202503750

Authors: Zhi‐Jie Niu, Bogdan R. Brutiu, Margaux Riomet, Daniel Kaiser, Nuno Maulide

Institution: University of Vienna

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funders: Austrian Science Fund, European Research Council