213700-77-7Relevant academic research and scientific papers
Stereoselective synthesis of 2e-phenyl-4e-hydroxy-1-azaspiro[5.5]undecane
Varlamov,Zubkov,Chernyshev,Kuznetsov,Pal'ma
, p. 69 - 72 (1998)
6-Phenylspiro(1-aza-7-oxabicyclo[2.2.1]heptane-2-cyclohexane) was synthesized by cyclization of N-benzylidene-1-allyl-1-cyclohexylamine N-oxide, and its reduction splitting yielded 2e-phenyl-4e-hydroxy-1-azaspiro[5.5]undecane. 1998 Plenum Publishing Corporation.
Concise synthesis of α-trisubstituted amines from ketones using n -methoxyamines
Kurosaki, Yusuke,Shirokane, Kenji,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka
supporting information; experimental part, p. 2098 - 2101 (2012/06/18)
Three-component allylation and cyanation utilizing a ketone and an N-methoxyamine are reported. The high nucleophilicity of the N-methoxyamine and high electrophilicity of the corresponding iminium ion enable the concise synthesis of α-trisubstituted amin
An improved and stereoselective route to all-cis-2,6-disubstituted 4-hydroxypiperidines from accessible 4-substituted 4-N-benzylaminobut-1-enes
Varlamov, Alexey,Kouznetsov, Vladimir,Zubkov, Fedor,Chernyshev, Alexey,Shurupova, Olga,Vargas Mendez, Leonor Y.,Palma Rodriguez, Alirio,Rivero Castro, Juliette,Rosas-Romero, Alfredo J.
, p. 771 - 783 (2007/10/03)
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.
