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A stereoselective approach for the total synthesis of [2(S)-phenyl-propionyl]-2-piperidinone-3-(R)-yl-ester and its diastereomer

✍ Scribed by Krishna, Palakodety Radha; Arun Kumar, Pendyala Venkata; Mallula, Venkata Satyanarayana; Ramakrishna, Kallaganti V.S.

Book ID
121712655
Publisher
Elsevier Science
Year
2013
Tongue
French
Weight
249 KB
Volume
69
Category
Article
ISSN
0040-4020

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A novel approach for the asymmetric synthesis of (3S,4R)-3-amino-4-alkyl-2-piperidinones: conformationally constrained dipeptides
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A straightforward method is developed for the synthesis of enantiopure (3S,4R)-3-amino-4-alkyl-2-piperidinone derivatives, six-membered lactam-bridged dipeptides, via highly diastereofacial selective 1,4-addition of organocuprate to the chiral oxazolidine a,b-unsaturated ester 1 as the key step.