Asymmetric conjugate reductions with samarium diiodide: Asymmetric synthesis of (2S,3R)- And (2S,3S)-[2-2H,3-2H]-leucine-(S)- phenylalanine dipeptides and (2S,3R)-[2-2H,3-2H]- phenylalanine methyl ester

Stephen G. Davies*, Humberto Rodríguez-Solla, Juan A. Tamayo, Andrew R. Cowley, Carmen Concellón, A. Christopher Garner, Alastair L. Parkes, Andrew D. Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

The highly diastereoselective samarium diiodide and D2O-promoted conjugate reduction of homochiral (E)- and (Z)-benzylidene and isobutylidene diketopiperazines (E)-5,7 and (Z)-6,8 has been demonstrated. This methodology allows the asymmetric synthesis of methyl (2S,3R)-dideuteriophenylalanine 27 in ≥95% de and >98% ee, and (2S,3R)- or (2S,3S)-dideuterioleucine-(S)- phenylalanine dipeptides 37 and 38 in moderate de, 66% and 74% respectively. A mechanism is proposed to account for this process.

Original languageEnglish
Pages (from-to)1435-1447
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume3
Issue number8
DOIs
Publication statusPublished - 21 Apr 2005

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