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

Stephen G. Davies*, Humberto Rodríguez-Solla, Juan A. Tamayo, A. Christopher Garner, Andrew D. Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2502-2503
Number of pages2
JournalChemical Communications
Volume10
Issue number21
DOIs
Publication statusPublished - 7 Nov 2004

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