Gold-Catalyzed Regioselective Hydration of Homopropargyl Alcohols Followed by Diastereoselective Reduction: An Easy Access to cis 2,5-Disubstituted Tetrahydrofurans

Title: Gold-Catalyzed Regioselective Hydration of Homopropargyl Alcohols Followed by Diastereoselective Reduction: An Easy Access to cis 2,5-Disubstituted Tetrahydrofurans

Volume: 6 Issue: 8

Author(s): Thi Xuan Mai Nguyen, Blandine Seon-Meniel, Jean-Christophe Jullian and Bruno Figadere

Affiliation:

Keywords: Regioselective hydration, diastereoselective reduction, natural products, cascade reactions

Abstract: A gold (III)-catalyzed hydration of homopropargyl alcohols led to the corresponding γ-hydroxy ketones, which were directly reduced by Ph3SiH in the presence of a Lewis acid, to afford the expected 2,5-disubstituted tetrahydrofurans as a diastereomeric mixture. NMR analysis of the compounds so obtained allowed us to confirm that the cis isomers were the major isomers that can be used for the preparation of new products.

Cite this article as:

Nguyen Xuan Mai Thi, Seon-Meniel Blandine, Jullian Jean-Christophe and Figadere Bruno, Gold-Catalyzed Regioselective Hydration of Homopropargyl Alcohols Followed by Diastereoselective Reduction: An Easy Access to cis 2,5-Disubstituted Tetrahydrofurans, Letters in Organic Chemistry 2009; 6 (8) . https://dx.doi.org/10.2174/157017809790442989