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Issue 43, 2012
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Conjugate hydrotrifluoromethylation of α,β-unsaturated acyl-oxazolidinones: synthesis of chiral fluorinated amino acids

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Abstract

A novel conjugate hydrofluoroalkylation of α,β-unsaturated acyl-oxazolidinones is described. Using this method, enantiomerically pure β-trifluoromethylated amino acids were prepared. Trifluorovaline and trifluoroisoleucine were incorporated into peptides and found to show extremely low α-helix propensities.

Graphical abstract: Conjugate hydrotrifluoromethylation of α,β-unsaturated acyl-oxazolidinones: synthesis of chiral fluorinated amino acids

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Publication details

The article was received on 14 Sep 2012, accepted on 25 Sep 2012 and first published on 26 Sep 2012


Article type: Communication
DOI: 10.1039/C2OB26810H
Citation: Org. Biomol. Chem., 2012,10, 8583-8586
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    Conjugate hydrotrifluoromethylation of α,β-unsaturated acyl-oxazolidinones: synthesis of chiral fluorinated amino acids

    H. Erdbrink, I. Peuser, U. I. M. Gerling, D. Lentz, B. Koksch and C. Czekelius, Org. Biomol. Chem., 2012, 10, 8583
    DOI: 10.1039/C2OB26810H

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