Issue 8, 2005
From the journal:

Organic & Biomolecular Chemistry

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,*a   Humberto Rodríguez-Solla,a   Juan A. Tamayo,a   Andrew R. Cowley,a   Carmen Concellón,a   A. Christopher Garner,a   Alastair L. Parkesa  and  Andrew D. Smitha  

* Corresponding authors

a Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, UK
E-mail: steve.davies@chem.ox.ac.uk

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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Article information

DOI
https://doi.org/10.1039/B500566C
Article type
Paper
Submitted
13 Jan 2005
Accepted
22 Feb 2005
First published
17 Mar 2005

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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