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From Propargylic Amides to Functionalized Oxazoles: Domino Gold Catalysis/Oxidation by Dioxygen

A. Stephen K. Hashmi*, Maria Camila Blanco Jaimes, Andreas M. Schuster and Frank Rominger

*Organisch-Chemisches Institut, Ruprecht-Karls-Universitšt Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Email: hashmihashmi.de

A. S. K. Hashmi, M. C. B. Jaimes, A. M. Schuster, F. Rominger, J. Org. Chem., 2012, 77, 6394-6408.

DOI: 10.1021/jo301288w (free Supporting Information)


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Abstract

A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. A subsequent autoxidation to hydroperoxides bearing the heteroaromatic oxazoles followed by reduction to the corresponding alcohols with sodium borohydride enables a highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles.

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Key Words

Oxazolines, Oxazoles, Oxygen, Sodium Borohydride


ID: J42-Y2012-2400