Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers

Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers Full article

Journal

Research on Chemical Intermediates
ISSN: 0922-6168 , E-ISSN: 1568-5675

Output data

Year: 2020, Volume: 46, Number: 2, Pages: 1183-1199 Pages count : 17 DOI: 10.1007/s11164-019-04027-4

Authors

Vereshchagin Anatoly N. ¹ , Karpenko Kirill A. ¹ , Elinson Michail N. ¹ , Goloveshkin Alexander S. ² , Dorofeeva Evgeniya O. ¹ , Egorov Mikhail P. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow, Russian Federation 119991
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Vaviliva Str., 28, Moscow, Russian Federation 119991

A novel four-component diastereoselective synthesis of polysubstituted 2-piperidinones is reported. The Michael addition–Mannich cascade of benzylidenemalononitriles or benzylidenecyanoacetates, dialkyl malonates, aromatic aldehydes and ammonium acetate in alcohols provides convenient access to alkyl (±)-5,5-dicyano-2-oxo-4,6-diarylpiperidine-3-carboxylates with three stereocenters in 66–92% or dialkyl (±)-2,4-diaryl-3-cyano-6-oxopiperidine-3,5-dicarboxylates with four stereocenters in 62–90%. The formation of products was highly stereoselective, with only one diastereomer formed. Ammonium acetate plays a dual role, acting as a base and as a nitrogen source. Structures of the synthesized compounds were confirmed by 1H NMR, 13C NMR, IR, elemental analysis and mass spectral studies. The formation of a single diastereomer was confirmed by singe-crystal X-ray diffraction studies.

Vereshchagin A.N. , Karpenko K.A. , Elinson M.N. , Goloveshkin A.S. , Dorofeeva E.O. , Egorov M.P.
Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers
Research on Chemical Intermediates. 2020. V.46. N2. P.1183-1199. DOI: 10.1007/s11164-019-04027-4 WOS Scopus OpenAlex

Web of science:	WOS:000491744600002
Scopus:	2-s2.0-85074652842
OpenAlex:	W2980567857

DB	Citing
OpenAlex	12
Scopus	10
Web of science	10