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

✍ Scribed by Juliette Martin; Marie-Claire Lasne; Jean-Christophe Plaquevent; Lucette Duhamel

Book ID
104258014
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
126 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Enantioselective protonation was applied on amide enolates la and 2a, derived from piperidine-2carboxylic acid. High enantioselectivity was obtained with diamine (+)-3, as chiral source, and in presence of LiBr. Up to 95Β±1% ee for amide 1 and >99% for amide 2 were reached. Moreover, (S)-I and (R)-I were obtained with 89% and 93% ee using (+) and (-) ephedrine respectively.

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