Synthesis of sulfonyl 2-aryl-5-methylenyltetrahydropyrans

Meng-Yang Chang; Kuan-Ting Chen

doi:10.1039/d3ra06370d

Synthesis of sulfonyl 2-aryl-5-methylenyltetrahydropyrans

RSC Adv. 2023 Oct 13;13(43):29894-29903. doi: 10.1039/d3ra06370d. eCollection 2023 Oct 11.

Authors

Meng-Yang Chang^{1

2

3}, Kuan-Ting Chen¹

Affiliations

¹ Department of Medicinal and Applied Chemistry, Kaohsiung Medical University Kaohsiung 807 Taiwan mychang@kmu.edu.tw.
² Department of Medical Research, Kaohsiung Medical University Hospital Kaohsiung 807 Taiwan.
³ NPUST College of Professional Studies, National Pingtung University of Science and Technology Pingtung 912 Taiwan.

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.