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Gold-Catalyzed Synthesis of Alkylidene 2-Oxazolidinones and 1,3-Oxazin-2-ones

Rocío Robles-Machín, Javier Adrio* and Juan Carlos Carretero*

*Departamento de Química Orgnica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Email: javier.adriouam.es, juancarlos.carreterouam.es

R. Robles-Machin, J. Adrio, J. C. Carretero, J. Org. Chem., 2006, 71, 4951-4955.

DOI: 10.1021/jo060520y (free Supporting Information)


Abstract

Various N-Boc-protected alkynylamines are converted into the corresponding alkylidene 2-oxazolidinones or 2-oxazinones under very mild reaction conditions in the presence of a cationic Au(I) complex in high yield regardless of the substitution at nitrogen and alkyne terminus.

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proposed mechanism



Key Words

2-Oxazolidinones, 1,3-Oxazin-2-ones


ID: J42-Y2006-1840