An improved and stereoselective route to all-cis-2,6-disubstituted 4-hydroxypiperidines from accessible 4-substituted 4-N-benzylaminobut-1-enes

The reaction between allylmagnesium bromide and imines 5a-l leads to the corresponding 4-substituted 4-N-benzylaminobut-1-enes 6a-1, which were oxidized in a regioselective manner to the alkenylnitrones 7a-l. The intramolecular 1,3-dipolar cycloaddition of these nitrones gave 2-spiroannulated or 2-substituted 6-exo-phenyl-1-aza-7-oxabicyclo[2.2.1]heptanes 8a-j. Reductive cleavage of the N-O bond of the obtained bicycles afforded the diverse substituted 4-hydroxypiperidines 9a-h in good yields. This stereoselective approach allowed the preparation of all-cis-4-hydroxy-6-phenyl-2-nonylpiperidine (9i), a close analogue of dendrobatid frog alkaloid 241D.

Авторы
Varlamov A. 1 , Kouznetsov V.2 , Zubkov F. 1 , Chernyshev A. 1 , Shurupova O. 1 , Vargas Méndez L.Y. , Palma Rodríguez A. , Rivero Castro J. , Rosas-Romero A.J.3
Редакторы
-
Журнал
Издательство
-
Номер выпуска
6
Язык
Английский
Страницы
771-783
Статус
Опубликовано
Подразделение
-
DOI
-
Номер
-
Том
-
Год
2002
Организации
  • 1 Department of Organic Chemistry, Russian Peoples Friendship Univ., 3 Ordzhonikidze St., 117419 Moscow, Russian Federation
  • 2 Research Center for Biomolecules, Laboratory of Fine Organic Synthesis, School of Chemistry, Industrial University of Santander, A.A. 678, Bucaramanga, Colombia
  • 3 Department of Chemistry, Simon Bolivar University, Caracas 1080A, Venezuela
Ключевые слова
1-aza-7-oxabicyclo[2.2.1]heptanes; 4-hydroxy-2-spiropiperidines; 4-hydroxypiperidines; Homoallylamines; Nitrones; Stereoselective intramolecular 1,3-dipolar cycloadditions
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/198/