Diastereocontrolled reduction of cyclic β-enaminones. A new diastereoselective route to 2,6-disubstituted piperidines

A new diastereoselective synthesis of 2,6-disubstituted piperidinic alkaloids is presented. Three natural compounds, the (−)-pinidinone 1a , the (+)-dihydropinidine 1b and the (−)-pinidinol 1c were prepared from optically pure (6 R)-6-methylpiperidin-2-one 2 . This method is based on the chemo- and...

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Bibliographic Details
Published in:Tetrahedron letters 2001-07, Vol.42 (28), p.4609-4611
Main Authors: Fréville, Stéphanie, Delbecq, Philippe, Thuy, Vu Moc, Petit, Huguette, Célérier, Jean Pierre, Lhommet, Gérard
Format: Article
Language:English
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Summary:A new diastereoselective synthesis of 2,6-disubstituted piperidinic alkaloids is presented. Three natural compounds, the (−)-pinidinone 1a , the (+)-dihydropinidine 1b and the (−)-pinidinol 1c were prepared from optically pure (6 R)-6-methylpiperidin-2-one 2 . This method is based on the chemo- and diastereocontrolled reductions of an exocyclic β-enamino ketone. A new diastereoselective synthesis of 2,6-disubstituted piperidinic alkaloids is presented. Three natural compounds, the (−)-pinidinone 1a , the (+)-dihydropinidine 1b and the (−)-pinidinol 1c were prepared from optically pure (6 R)-6-methylpiperidin-2-one 2 . This method is based on the diastereoselective reductions of an exocyclic β-enamino ketone.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)00770-5