Related Experiment Video
Updated: Aug 19, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Highly diastereoselective synthesis of tetrahydrofurans via Lewis acid-catalyzed cyclopropane/aldehyde cycloadditions
Patrick D Pohlhaus1, Jeffrey S Johnson
1Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
Abstract:
A one-step procedure for the preparation of 2,5-disubstituted tetrahydrofurans from donor-acceptor cyclopropanes and aldehydes has been developed. In the presence of a catalytic amount of Sn(OTf)(2), cyclopropanes bearing an aryl or conjugated donor substituent vicinal to a malonyl diester group undergo cycloadditions with diverse conjugated aldehydes furnishing tetrahydrofurans with high cis diastereoselectivity. This method is useful for the preparation of regiodefined tetrahydrofurans.
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

