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

Statistics

Number of views

15 (0 by ULiège)

Number of downloads

0 (0 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

.
Brown, E.G., Ring Nitrogen and Key Biomolecules: The Biochemistry of N-Heterocycles, 1998, Dordrecht, The Netherlands.
Fotsch, C., J. Med. Chem. 55 (2012), 6002–6020.
E.Davioud-Charvet,I.N.Wenzel,T.J.J.Mueller,G.Hanquet,D.A.Lanfranchi,F.Leroux,T.Gendron, WO2011033115A2, 2011.
Ingall, A.H., Compr. Heterocycl. Chem., 1984, 885–942.
Sankarapapavinasam, S., Pushpanaden, F., Ahmed, M., Corros. Sci. 32 (1991), 193–203.
Chen, C.H., Reynolds, G.A., Luss, H.R., Perlstein, J.H., J. Org. Chem. 51 (1986), 3282–3289.
Rule, N.G., Detty, M.R., Kaeding, J.E., Sinicropi, J.A., J. Org. Chem. 60 (1995), 1665–1673.
M.R.Detty,J.A.Sinicropi,R.J.Cowdery-Corvan,R.H.Young, Electrophotographic Elements and Soluble Cyclic Sulfone Electron Transport Agents, EP0691579A1, 1996.
El-Ghanam, A.M., Phosphorus Sulfur Silicon Relat. Elem. 181 (2006), 1419–1425.
Amutha, P., Nagarajan, S., Helv. Chim. Acta 93 (2010), 430–434.
Chaykovsky, M., Lin, M., Rosowsky, A., Modest, E.J., J. Med. Chem. 16 (1973), 188–191.
Jayabharathi, J., Thanikachalam, V., Thangamani, A., Padmavathy, M., Med. Chem. Res. 16 (2007), 266–279.
Gopalakrishnan, M., Thanusu, J., Kanagarajan, V., J. Enzyme Inhib. Med. Chem. 24 (2009), 669–675.
Parthiban, P., Aridoss, G., Rathika, P., Ramkumar, V., Kabilan, S., Bioorg. Med. Chem. Lett. 19 (2009), 2981–2985.
Arndt, F., Nachtwey, P., Pusch, J., Ber. Dtsch. Chem. Ges. 58 (1925), 1633–1644.
Chen, C.H., Reynolds, G.A., Van Allan, J.A., J. Org. Chem. 42 (1977), 2777–2778.
Ramalingam, K., Berlin, K.D., Satyamurthy, N., Sivakumar, R., J. Org. Chem. 44 (1979), 471–477.
Burnett, J.F., Zahler, R.E., Chem. Rev. 49 (1951), 273–412.
The racemic (±)-trans isomer will be further abbreviated to trans isomer.
Krein, E.B., Aizenshtat, Z., J. Org. Chem. 58 (1993), 6103–6108.
.
Jones, R.A., Quaternary Ammonium Salts: Their Use in Phase-Transfer Catalysed Reactions, 2001, Academic Press, San Diego.
Nakayama, J., Machida, H., Hoshino, M., Tetrahedron Lett. 24 (1983), 3001–3004.
Compound 1a was used as a prototypical substrate for preliminary investigations as the resulting two diastereoisomers were clearly characterized and could be separated and quantified by HPLC and NMR spectroscopy, see the Supporting Information.
Baxter, C.A.R., Whiting, D.A., J. Chem. Soc. C, 1968, 1174–1178.
CCDC-1031022 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
Giggenbach, W., Inorg. Chem. 10 (1971), 1333–1338.