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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.

Original publication

DOI

10.1039/b408257e

Type

Journal article

Journal

Chem Commun (Camb)

Publication Date

07/11/2004

Pages

2502 - 2503

Keywords

Iodides, Molecular Structure, Oxidation-Reduction, Phenylpropionates, Samarium, Stereoisomerism