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Issue 23, 2004
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Asymmetric synthesis of 2-alkyl- and 2-aryl-3-aminopropionic acids (β2-amino acids) from (S)-N-acryloyl-5,5-dimethyloxazolidin-2-one SuperQuat derivatives

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Abstract

Conjugate addition of lithium amides to (S)-N-acryloyl- or (S)-N-2′-alkylacryloyloxazolidinones and alkylation or protonation of the resulting enolates with 2-pyridone respectively provides a highly stereoselective and product complementary route to a range of (R)- and (S)-2-alkyl-3-aminopropionic acids in good yield and in high ee.

Graphical abstract: Asymmetric synthesis of 2-alkyl- and 2-aryl-3-aminopropionic acids (β2-amino acids) from (S)-N-acryloyl-5,5-dimethyloxazolidin-2-one SuperQuat derivatives

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Publication details

The article was received on 19 Jul 2004, accepted on 23 Aug 2004 and first published on 22 Oct 2004


Article type: Communication
DOI: 10.1039/B410938D
Citation: Chem. Commun., 2004,0, 2778-2779
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    Asymmetric synthesis of 2-alkyl- and 2-aryl-3-aminopropionic acids (β2-amino acids) from (S)-N-acryloyl-5,5-dimethyloxazolidin-2-one SuperQuat derivatives

    J. E. Beddow, S. G. Davies, A. D. Smith and A. J. Russell, Chem. Commun., 2004, 0, 2778
    DOI: 10.1039/B410938D

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