Related Experiment Video
Updated: Jul 8, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Asymmetric [4+3] cycloadditions between benzofuranyldiazoacetates and dienes: formal synthesis of (+)-frondosin B
Jeremy P Olson1, Huw M L Davies
1Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260-3000, USA.
Abstract:
The reaction of benzofuranyldiazoacetates with 1,3-dienes catalyzed by the dirhodium tetracarboxylate Rh2(R-DOSP)4, generates formal [4+3] cycloadducts with >94% de and 91-98% ee. The reaction proceeds by a tandem cyclopropanation/Cope rearrangement followed by a stereoselective tautomerization. This methodology was extended to a formal synthesis of (+)-frondosin B.
More Related Videos
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Cycloaddition Reactions: Overview
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

