Tetrahedron p. 8447 - 8456 (1997)
Update date:2022-08-02
Topics:
Freville, Stephanie
Bonin, Martine
Celerier, Jean-Peirre
Husson, Henri-Philippe
Lhommet, Gerard
Quirion, Jean-Charles
Thuy, Vu Moc
(+) aid (-) trans-2,6-dimethylpiperidines 9 have been prepared from diastereomeric lactams 6 and 11, both available from (R)-(-)-phenylglycinol 4. Diastereoselective C-2 alkylation afforded oxazolidines 7 and 12. Reduction of 7 with LiAlH4 or NaBH4 led to trans-2,6-8 with total retention of configuration. When 12 was reduced with NaBH4, trans derivative 13a was isolated as the major isomer. A mechanism is proposed to explain the different results.
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