ASYMMETRIC-SYNTHESIS OF (-TRANS-2,6-DIMETHYLPIPERIDINES AND (-)-TRANS-2,6-DIMETHYLPIPERIDINES())

Authors
FREVILLE S BONIN M CELERIER JP HUSSON HP LHOMMET G QUIRION JC THUY VM
Citation
S. Freville et al., ASYMMETRIC-SYNTHESIS OF (-TRANS-2,6-DIMETHYLPIPERIDINES AND (-)-TRANS-2,6-DIMETHYLPIPERIDINES()), Tetrahedron, 53(25), 1997, pp. 8447-8456
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
25
Year of publication
1997
Pages
8447 - 8456
Database
ISI
SICI code
0040-4020(1997)53:25<8447:AO(A(>2.0.ZU;2-J
Abstract
(+) and (-) trans-2,6-dimethylpiperidines 9 have been prepared from di astereomeric lactams 6 and 11, both available from (R)-(-)-phenylglyci nol 4. Diastereoselective C-2 alkylation afforded oxazolidines 7 and 1 2. Reduction of 7 with LiAlH4 or NaBH4 led to trans-2,6-8 with total r etention of configuration; When 12 was reduced with NaBH4, irans deriv ative 13a was isolated as the major isomer. A mechanism is proposed to explain the different results. (C) 1997 Elsevier Science Ltd.