Issue 43, 2023, Issue in Progress

Synthesis of sulfonyl 2-aryl-5-methylenyltetrahydropyrans

Abstract

In this study, the present research describes a high-yield method for the synthesis of sulfonyl 2-aryl-5-methylenetetrahydropyrans by one-pot straightforward DABCO-promoted intramolecular Michael addition of β-sulfonyl styrene with 2-chloromethyl-1-propenol followed by intramolecular alkylation. This Baylis–Hillman-type pathway provides a highly effective stereoselective annulation by forming one carbon–oxygen bond and one carbon–carbon bond.

Graphical abstract: Synthesis of sulfonyl 2-aryl-5-methylenyltetrahydropyrans

Supplementary files

Article information

Article type
Paper
Submitted
19 Sep 2023
Accepted
06 Oct 2023
First published
13 Oct 2023
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2023,13, 29894-29903

Synthesis of sulfonyl 2-aryl-5-methylenyltetrahydropyrans

M. Chang and K. Chen, RSC Adv., 2023, 13, 29894 DOI: 10.1039/D3RA06370D

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements