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Issue 9, 2005
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On the activation of valerolactam with triflic anhydride: the synthesis of ω-trifluorosulfonamido dipeptides using a transpeptidation reaction under mild conditions

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Abstract

The activation of valerolactam with triflic anhydride is studied in detail, initially producing an O-triflated lactam, which rearranges, following the addition of base at higher temperatures, to an N-triflated derivative. This reacts with a series of nucleophiles to produce esters and amides, which are formally dipeptides of ω-amino acids.

Graphical abstract: On the activation of valerolactam with triflic anhydride: the synthesis of ω-trifluorosulfonamido dipeptides using a transpeptidation reaction under mild conditions

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Publication details

The article was received on 26 Nov 2004, accepted on 16 Feb 2005 and first published on 29 Mar 2005


Article type: Paper
DOI: 10.1039/B417779G
Citation: Org. Biomol. Chem., 2005,3, 1694-1701
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    On the activation of valerolactam with triflic anhydride: the synthesis of ω-trifluorosulfonamido dipeptides using a transpeptidation reaction under mild conditions

    N. Kuhnert, I. Clemens and R. Walsh, Org. Biomol. Chem., 2005, 3, 1694
    DOI: 10.1039/B417779G

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