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Construction of Chiral Piperidine Scaffold through an Enantioselective (8+3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Azaheptafulvenes

Year: 2026

Type: preprint

Abstract: An efficient synthesis of chiral piperidine derivatives via an enantioselective Brønsted base-catalyzed (8+3)-cycloaddition is reported. This strategy employs azaheptafulvenes, which undergo cycloaddition with donor-acceptor cyclopropanes serving as three-carbon building blocks, providing efficient access to a new class of chiral piperidine frameworks. The developed method enables the synthesis of a broad range of chiral piperidine derivatives fused to a seven-membered cycloheptatriene ring with high stereoselectivity, broad substrate scope, and excellent functional group tolerance. Furthermore, transformations of the obtained products were demonstrated, providing access to new chiral piperidine-based frameworks.

Source: ChemRxiv

DOI: 10.26434/chemrxiv.15008171/v1

Authors: Adam Cieśliński, Anna Skrzyńska, Gonzalo Blay, Carlos Vila, Lukasz Albrecht

Institutions: Lodz University of Technology, Institute of Organic Chemistry, Institute of Organic Chemistry, Universitat de València

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

OpenAlex ID: W7204899714

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