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DOI: 10.1055/s-0029-1219156
One-Pot Conversion of α-Amino Acids into β-Amino Aldehydes or 2-Acetoxyazetidines: Application to the Synthesis of Modified Peptides
Publication History
Publication Date:
22 December 2009 (online)
Abstract
A direct method for the transformation of α-amino acids into β-amino aldehydes or 2-acetoxyazetidines is described. This work was applied to the modification of peptides.
Key words
amino aldehydes - heterocycles - peptides - radical reactions - domino reactions
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The proposed stereochemistry was deduced from the value of the ¹H NMR coupling constants, which showed a cis relationship 2-H/3-Ha/4-H and a trans relationship 2-H/3-Hb and 4-H/3-Hb (J 3a = 6.6, 6.9 Hz, while J 3b = 3.8, 4.4 Hz).
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