Synthesis of sulfonyl 2-aryl-5-methylenyltetrahydropyrans

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. Thi...

Full description

Saved in:
Bibliographic Details
Published inRSC advances Vol. 13; no. 43; pp. 29894 - 2993
Main Authors Chang, Meng-Yang, Chen, Kuan-Ting
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 13.10.2023
The Royal Society of Chemistry
Subjects
Alkylation
Aromatic compounds
Carbon
Chemical reactions
Chemistry
Stereoselectivity
Synthesis
Online AccessGet full text

Cover

More Information
Summary: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. The one-pot construction of diversified sulfonyl 2-aryl-5-methylenetetrahydropyrans is developed by DABCO-promoted intramolecular Michael addition of β-sulfonyl styrene with 2-chloromethyl-1-propenol followed by intramolecular alkylation.
Bibliography:For ESI and crystallographic data in CIF or other electronic format see DOI
https://doi.org/10.1039/d3ra06370d
2279054-2279055
and
5m
Electronic supplementary information (ESI) available: Scanned photocopies of NMR spectral data for all compounds and X-ray analysis data of
5n
were supported. CCDC
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
content type line 23
ISSN:2046-2069
2046-2069
DOI:10.1039/d3ra06370d