Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers

Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers Full article

Journal

Mendeleev Communications
ISSN: 1364-551X , E-ISSN: 0959-9436

Output data

Year: 2022, Volume: 32, Number: 5, Pages: 629-631 Pages count : 3 DOI: 10.1016/j.mencom.2022.09.020

Authors

Iliyasov Taigib M. ¹ , Karpenko Kirill A. ¹ , Vinokurov Andrey D. ¹ , Fakhrutdinov Artem N. ¹ , Tyutin Alexander A. ² , Elinson Michail N. ¹ , Vereshchagin Anatoly N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
2	D. I. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russian Federation

The Michael–Mannich cascade cyclization of cyano olefins, ethyl 4,4,4-trifluoro-3-oxobutanoate, aromatic aldehydes and ammonium acetate provides convenient stereoselective formation of ethyl 5,5-dicyano-4,6-diaryl-2-hydroxy-2-(trifluoromethyl)piperidine-3-carboxylates with fourstereogenic centers and dialkyl 4,6-diaryl-5-cyano-2-hydroxy-2-(trifluoromethyl)piperidine-3,5-dicarboxylates with five stereogenic centers. Ammonium acetate plays dual role, acting as a base and as a nitrogen source.

Iliyasov T.M. , Karpenko K.A. , Vinokurov A.D. , Fakhrutdinov A.N. , Tyutin A.A. , Elinson M.N. , Vereshchagin A.N.
Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers
Mendeleev Communications. 2022. V.32. N5. P.629-631. DOI: 10.1016/j.mencom.2022.09.020 WOS Scopus OpenAlex

Web of science:	WOS:000874166100020
Scopus:	2-s2.0-85139344202
OpenAlex:	W4302759525

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OpenAlex	5
Scopus	3
Web of science	4