Related Experiment Video
Updated: Jun 18, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Synthesis of 3-vinyl-2,5-dihydrofuran ring system via enyne metathesis
Sophie Vuong1, M Mercedes Rodriguez-Fernandez, Brigitte Renoux
1Université de Poitiers, UMR 6514 CNRS, Synthèse et Réactivité des Substances Naturelles, 40 Avenue du Recteur Pineau, F-86022 Poitiers cedex, France.
Abstract:
An efficient route, starting from but-3-en-1,2-diol, is described to synthesize racemic diastereoisomeric (5-ethoxy-4-vinyl-2,5-dihydrofuran-2-yl) methanol derivatives. Acyclic enyne intermediates having the alkyne moiety directly connected to the asymmetric carbon atom of an acetal were obtained in two steps. These reactive substrates were then subjected to ruthenium-catalyzed enyne metathesis to produce the target compounds in racemic form. The relative configurations were determined by NOE proton NMR experiments. Similar strategy starting from (2S)-but-3-en-1,2-diol was proposed to provide pure enantiomers.
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Olefin Metathesis Polymerization: Overview
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

