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

Authors :: Davies SG
Rodríguez-Solla H
Tamayo JA
Garner AC
Smith AD
Source :: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2004 Nov 07 (21), pp. 2502-3. Date of Electronic Publication: 2004 Sep 08.
Publication Year :: 2004
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 in 93% de and 90% ee after deprotection, hydrolysis and N-acetylation.

Subjects :: Molecular Structure
Oxidation-Reduction
Stereoisomerism
Iodides chemistry
Phenylpropionates chemical synthesis
Samarium chemistry

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