Enantioselective protonation of amide enolates derived from piperidine-2-carboxylic acid

Enantioselective protonation was applied on amide enolates 1a and 2a, derived from piperidine-2-carboxylic acid. High enantioselectivity was obtained with diamine (+)- 3, as chiral source, and in presence of LiBr. Up to 95±1% ee for amide 1 and >99% for amide 2 were reached. Moreover, (S)- 1 and...

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Bibliographic Details
Published in:Tetrahedron letters 1997-10, Vol.38 (41), p.7181-7182
Main Authors: Martin, Juliette, Lasne, Marie-Claire, Plaquevent, Jean-Christophe, Duhamel, Lucette
Format: Article
Language:English
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Summary:Enantioselective protonation was applied on amide enolates 1a and 2a, derived from piperidine-2-carboxylic acid. High enantioselectivity was obtained with diamine (+)- 3, as chiral source, and in presence of LiBr. Up to 95±1% ee for amide 1 and >99% for amide 2 were reached. Moreover, (S)- 1 and (R)- 1 were obtained with 89% and 93% ee using (+) and (−) ephedrine respectively. The amides 1 or 2 have been prepared with high enantioselectivity by asymmetric protonation of their lithium enolates in the presence of a chiral amine.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01705-X