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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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Article information


Submitted
02 Jun 2004
Accepted
28 Jun 2004
First published
08 Sep 2004

Chem. Commun., 2004, 2502-2503
Article type
Communication

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, 2502
DOI: 10.1039/B408257E

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