Stereoselective Synthesis of Polysubstituted Tetrahydropyrans by Brønsted Acid‐Mediated Hydroxyalkoxylation of Silylated Alkenols-Reference-Cited by-同舟云学术

Stereoselective Synthesis of Polysubstituted Tetrahydropyrans by Brønsted Acid‐Mediated Hydroxyalkoxylation of Silylated Alkenols

Published:2024-05-03 Issue:7 Volume:13 Page:
ISSN:2193-5807
Container-title:Asian Journal of Organic Chemistry
language:en
Short-container-title:Asian J Org Chem

Author:

Díez‐Poza Carlos¹^ORCID,Val Patricia¹,López Enol²,Barbero Asunción¹^ORCID

Affiliation:

1. Department of Organic Chemistry Faculty of Science University of Valladolid (UVa) Campus Miguel Delibes 47011 Valladolid Spain.

2. Department of Organic Chemistry School of Engineering (EII) University of Valladolid (UVa) 47002 Valladolid Spain

Abstract

AbstractA convenient route for the preparation of tetrahydropyran (THP) derivatives with a quaternary and tertiary vicinal stereocenters is reported. The atom economy acid‐catalyzed cyclization of allylsilyl alcohols provided polysubstituted tetrahydropyrans in good yields and excellent diastereoselectivities (>95 : 5). In comparison with the traditional oxymercuration procedure, this approach resulted to be more efficient in both yield and stereocontrol.

Publisher

Wiley

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/ajoc.202400096

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