Approach to 3-(Cyclo)alkylpiperidines through 'sp3-sp3 via sp2-sp3' Coupling.

Autor: Subota, Andrii I., Grygorenko, Oleksandr O., Valter, Yevheniia B., Tairov, Maxim A., Artamonov, Oleksiy S., Volochnyuk, Dmitriy M., Ryabukhin, Sergey V.
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Zdroj: Synlett; 2015, Vol. 26 Issue 3, p408-411, 4p
Abstrakt: The idea of introducing (cyclo)alkyl substituents at the C-3 atom of the piperidine ring, that is, formal sp3-sp3 retrosynthetic disconnection, is implemented through a two-step reaction sequence including directed ortho metalation of a pyridine derivative and the subsequent quenching with a carbonyl compound, followed by catalytic hydrogenation. This robust but very efficient method allows for multigram preparation of sp3-rich 3-(cyclo)alkylpiperidines, which are valuable building blocks for medicinal chemistry and other areas. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index