New stereoselective syntheses of cis- and trans-2-methyl-4-arylpiperidines

Merschaert, A.;Delhaye, L.;Kestemont, JP.;Brione, W.;Vanmarsenille, M;et.al.
(2003) Tetrahedron Letters — Vol. 44, n° 24, p. 4531-4534 (2003)

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Authors
  • Merschaert, A.
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  • Delhaye, L.
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  • Kestemont, JP.
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  • Brione, W.
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  • Vanmarsenille, M
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Abstract
A stereoselective approach has been developed for the synthesis of cis- and trans-2-methyl-4-arylpiperidines from a common intermediate. The Ni-catalyzed hydrogenolysis of N-Boc-2-methyl-4-aryl-4-piperidinols, obtained by addition of organometallic reagents on N- Boc-2-methyl-4-piperidone, afforded the trans derivatives with Lip to 95% selectivity whereas the corresponding cis isomers were obtained in the presence of palladium catalysts. (C) 2003 Elsevier Science Ltd. All rights reserved.
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Merschaert, A., Delhaye, L., Kestemont, JP., Brione, W., Delbeke, P., Mancuso, V., Napora, F., Diker, K., Giraud, D., & Vanmarsenille, M. (2003). New stereoselective syntheses of cis- and trans-2-methyl-4-arylpiperidines. Tetrahedron Letters, 44(24), 4531-4534. https://doi.org/10.1016/S0040-4039(03)01021-9 (Original work published 2003)