136936-07-7Relevant academic research and scientific papers
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.
SYNTHESIS OF METHYL-SUBSTITUTED 1,2,4,5-TETRAHYDRO-3H-SPIRO
Kuznetsov, V. V.,Lantsetov, S. V.,Aliev, A. E.,Varlamov, A. V.,Prostakov, N. S.
, p. 61 - 65 (2007/10/02)
5-Methyl and 1,5-dimethyl-1,2,4,5-tetrahydro-3H-spiro and their cyclohexane and methylcyclohexane analogs were obtained by the intramolecular cyclization of the corresponding 1-allyl-1-N-benzyl(α-phenylethyl)aminocycloalkanes.The configuration of these products was established.
