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Issue 21, 2004
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Diastereoselective conjugate reduction with samarium diiodide: asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate

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Abstract

A highly diastereoselective conjugate reduction using SmI2 and D2O has been demonstrated on a homochiral benzylidene diketopiperazine template, giving methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate 12 in 93% de and 90% ee after deprotection, hydrolysis and N-acetylation.

Graphical abstract: Diastereoselective conjugate reduction with samarium diiodide: asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate

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Publication details

The article was received on 02 Jun 2004, accepted on 28 Jun 2004 and first published on 08 Sep 2004


Article type: Communication
DOI: 10.1039/B408257E
Citation: Chem. Commun., 2004,0, 2502-2503
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    Diastereoselective conjugate reduction with samarium diiodide: asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate

    S. G. Davies, H. Rodríguez-Solla, J. A. Tamayo, A. C. Garner and A. D. Smith, Chem. Commun., 2004, 0, 2502
    DOI: 10.1039/B408257E

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