| Autor: |
Davies SG; Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, UK. steve.davies@chem.ox.ac.uk, Rodriguez-Solla H, Tamayo JA, Cowley AR, Concellon C, Garner AC, Parkes AL, Smith AD |
| Jazyk: |
angličtina |
| Zdroj: |
Organic & biomolecular chemistry [Org Biomol Chem] 2005 Apr 21; Vol. 3 (8), pp. 1435-47. Date of Electronic Publication: 2005 Mar 17. |
| DOI: |
10.1039/b500566c |
| Abstrakt: |
The highly diastereoselective samarium diiodide and D(2)O-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 > or = 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. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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