Diastereoselective conjugate reduction with samarium diiodide: asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate.
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.
Davies
Stephen G
SG
The Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK OX1 3TA. steve.davies@chem.ox.ac.uk
Rodríguez-Solla
Humberto
H
Tamayo
Juan A
JA
Garner
A Christopher
AC
Smith
Andrew D
AD
D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010666:Phenylpropionates / Q000138:chemical synthesis*; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism
D007454:Iodides; D010666:Phenylpropionates; C506112:methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate; D012493:Samarium; C409809:samarium diiodide