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Copper-Catalyzed One-Pot Synthesis of N-Aryl Oxazolidinones from Amino Alcohol Carbamates

William Mahy, Pawel K. Plucinski and Christopher G. Frost*

*Department of Chemistry, Centre for Sustainable Chemical Technologies, University of Bath, Claverton Down, Bath, BA2 7AY, U.K., Email: c.g.frostbath.ac.uk

W. Mahy, P. K. Plucinski, C. G. Frost, Org. Lett., 2014, 16, 5020-5021.

DOI: 10.1021/ol502322c (free Supporting Information)


Abstract

An efficient sequential intramolecular cyclization of amino alcohol carbamates followed by Cu-catalyzed cross-coupling with aryl iodides under mild conditions gives N-aryl oxazolidinones in good yields. The reaction tolerated aryl iodides containing functionalities such as nitriles, ketones, ethers, and halogens. Heteroaryl iodides and substituted amino alcohol carbamates were can also be transformed.


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Key Words

Oxazolidinones


ID: J54-Y2014