One-pot highly diastereoselective five-component synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidines with four and five stereogenic centers

One-pot highly diastereoselective five-component synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidines with four and five stereogenic centers Full article

Journal

Arkivoc
ISSN: 1551-7012 , E-ISSN: 1551-7004

Output data

Year: 2022, Volume: 2022, Number: 9, Pages: 119-132 Pages count : 14 DOI: 10.24820/ark.5550190.p011.867

Authors

Vereshchagin Anatoly N. ¹ , Iliyasov Taygib ¹ , Karpenko Kirill ¹ , Vinokurov Andrey ¹ , Tyutin Alexander ^1,2 , Elinson Michail ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
2	Mendeleev University of Chemical Technology of Russia, 125047, Miusskaya square 9, Moscow, Russian Federation

The Knoevenagel–Michael–Mannich–cyclization cascade of aldehydes, cyano-containing C-H acids, ethyl 4,4,4-trifluoro-3-oxobutanoate and ammonium acetate provided convenient stereoselective formation of ethyl 5,5-dicyano-4,6-diaryl-2-hydroxy-2-(trifluoromethyl)pi-peridine-3-carboxylates with four stereogenic centers and dialkyl 4,6-diaryl-5-cyano-2-hydroxy-2-(trifluoromethyl)piperidine-3,5-dicarboxylates with five stereogenic centers. The stereoselective formation of individual diastereomers was shown. The configuration of diastereomers was confirmed by NMR spectra and X-ray diffraction analysis. Ammonium acetate played dual role, acting as a base and as a nitrogen source

Vereshchagin A.N. , Iliyasov T. , Karpenko K. , Vinokurov A. , Tyutin A. , Elinson M.
One-pot highly diastereoselective five-component synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidines with four and five stereogenic centers
Arkivoc. 2022. V.2022. N9. P.119-132. DOI: 10.24820/ark.5550190.p011.867 Scopus OpenAlex

Scopus:	2-s2.0-85147872417
OpenAlex:	W4306907105

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