Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers Научная публикация
Журнал |
Research on Chemical Intermediates
ISSN: 0922-6168 , E-ISSN: 1568-5675 |
||||
---|---|---|---|---|---|
Вых. Данные | Год: 2020, Том: 46, Номер: 2, Страницы: 1183-1199 Страниц : 17 DOI: 10.1007/s11164-019-04027-4 | ||||
Авторы |
|
||||
Организации |
|
Реферат:
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.
Библиографическая ссылка:
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
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
Идентификаторы БД:
Web of science: | WOS:000491744600002 |
Scopus: | 2-s2.0-85074652842 |
OpenAlex: | W2980567857 |