Work

Unlocking the Synthetic Potential of HMF Derivatives in Catalytic Asymmetric Aza‐Piancatelli Rearrangement

Year: 2026

Type: article

Abstract: The Piancatelli rearrangement of (2‐furyl)carbinols has now become an efficient synthetic method for the construction of cyclopentenones. However, the use of substrates bearing a C‐5 substitution on the furan moiety of (2‐furyl)carbinols remains largely underexplored. In this study, we employed 5‐hydroxymethylfurfural (HMF) derivatives as substrates, obtained in a single step from HMF, a key platform molecule and flagship compound for biomass valorization, to achieve the first catalytic asymmetric aza ‐Piancatelli rearrangement of C‐5‐substituted (2‐furyl)carbinols. The resulting aza ‐cyclopentenones, which feature two contiguous stereogenic centers including one quaternary center, were obtained in total regio‐ and diastereoselectivities and in enantioselective manner up to 92.4:7.6 er.

Source: ChemistryEurope

DOI: 10.1002/ceur.70275

Authors: Clémentine Mayet, Thibault Mattera, Pascal Retailleau, Jean‐François Betzer

Institutions: Centre National de la Recherche Scientifique, Institut de Chimie des Substances Naturelles, Université Paris-Saclay

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Agence Nationale de la Recherche, Centre National de la Recherche Scientifique

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