Related Experiment Video
Updated: May 13, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
General one-step access to unsymmetric propargylic acetals via alcohol functionalization with allenyl ethers
1School of Pharmaceutical Sciences, Guizhou Engineering Laboratory for Synthetic Drugs, Guizhou University Guiyang Guizhou 550025 China szhe@gzu.edu.cn.
Abstract:
We report a straightforward and robust protocol for synthesizing unsymmetric propargylic acetals through single-step alkoxypropargylation of aliphatic alcohols. This method employs allenyl ethers and hypervalent iodine reagents to achieve direct functionalization under mild conditions, producing 26 distinct acetals in 60-94% yields. The reaction's broad substrate compatibility accommodates diverse hydroxyl-containing molecules, offering a versatile and scalable platform for installing alkynyl moieties in complex molecular architectures.
Related Concept Videos
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
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.
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

