Diastereoselective Synthesis of 2,6-Diaryltetrahydrothiopyran-4-ones by Phase-Transfer Catalysis

Configuration determination; Diastereoselectivity; Michael addition; Phase-transfer catalysis; Sulfur heterocycles; Synthetic methods; Organic Chemistry

Abstract :

[en] Two efficient phase-transfer-catalyzed protocols for the diastereoselective synthesis of cis and trans isomers of 2,6-diaryltetrahydrothiopyran-4-ones (2,6-DATHTPs) have been developed. In a study of the scope of the reactions, differently substituted 2,6-DATHTPs were successfully accessed in high yields and diastereomeric excessses on both experimental and preparative scales.

Research Center/Unit :

European School of Chemistry, Polymers and Materials, Bioorganic and Medicinal Chemistry, UMR CNRS 7509

Disciplines :

Chemistry

Author, co-author :

Gendron, Thibault ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique-nucléaire ; European School of Chemistry, Polymers and Materials, Bioorganic and Medicinal Chemistry, UMR CNRS 7509, France

Kessedjian, Hripsimée; European School of Chemistry, Polymers and Materials, Bioorganic and Medicinal Chemistry, UMR CNRS 7509, France

Davioud-Charvet, Elisabeth; European School of Chemistry, Polymers and Materials, Bioorganic and Medicinal Chemistry, UMR CNRS 7509, France

Lanfranchi, Don Antoine; European School of Chemistry, Polymers and Materials, Bioorganic and Medicinal Chemistry, UMR CNRS 7509, France

Language :

English

Title :

Diastereoselective Synthesis of 2,6-Diaryltetrahydrothiopyran-4-ones by Phase-Transfer Catalysis

Publication date :

March 2015

Journal title :

European Journal of Organic Chemistry

ISSN :

1434-193X

eISSN :

1099-0690

Publisher :

John Wiley and Sons Inc

Volume :

2015

Issue :

Pages :

1790 - 1796

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.201403516

Funders :

ANR - Agence Nationale de la Recherche

Funding number :

ANR-11-LABX-0024

Funding text :

This work was supported by the Centre National de la Recherche Scientifique (CNRS) (UMR7509, grant to E. D.-C.) and the Laboratoire d'Excellence (LabEx) ParaFrap (grant LabEx ParaFrap ANR-11-LABX-0024 to E. D.-C.). T. G. is grateful to the French Ministry of Research for funding his Ph. Dissertation. The authors would like to thank Xavier Martin-Benlloch and Dr. Kerstin Sander for their precious help and advice.

Available on ORBi :

since 22 June 2023

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