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Issue 8, 2005
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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

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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.

Graphical abstract: 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

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Publication details

The article was received on 13 Jan 2005, accepted on 22 Feb 2005 and first published on 17 Mar 2005


Article type: Paper
DOI: 10.1039/B500566C
Citation: Org. Biomol. Chem., 2005,3, 1435-1447
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    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

    S. G. Davies, H. Rodríguez-Solla, J. A. Tamayo, A. R. Cowley, C. Concellón, A. C. Garner, A. L. Parkes and A. D. Smith, Org. Biomol. Chem., 2005, 3, 1435
    DOI: 10.1039/B500566C

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