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Iodine-Mediated Oxidative Coupling of Hydroxamic Acids with Amines towards a New Peptide-Bond Formation

Muniyappa Krishnamurthy, T. M. Vishwanatha, Nageswara Rao Panguluri, V. Panduranga, Vommina V. Sureshbabu*

*Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore 560 001, India, Email: hariccbhotmail.com, sureshbabuvomminarediffmail.com

M. Krishnamurthy, T. M. Vishwanatha, N. R. Panguluri, V. Panduranga, V. V. Sureshbabu, Synlett, 2015, 26, 2565-2569.

DOI: 10.1055/s-0035-1560266 (free Supporting Information)


Abstract

Formation of unstable but reactive acyl nitroso intermediates from Nα-protected hydroxamic acids in the presence of iodine and DMSO enables an efficient and straightforward coupling with an amino component to yield dipeptide esters.

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Key Words

Nα-protected amino hydroxamic acids, amino acid esters, amides, oxidative acylation, acyl nitroso intermediate, iodine, DMSO


ID: J60-Y2015