Oxazolidinones are a family of compounds which have shown to be valuable structural motifs in a number of applications, from organocatalysts and chiral auxiliaries to polymers and antipsychotics. More recently, N-aryl oxazolidinones have emerged as a critical structure in a family of molecules which show antibiotic properties, most notably Linezolid.With the emerging interest in a particular structure comes the need for cleaner, simpler and more efficient methods towards their synthesis. Ideally, new methods would employ mild conditions, readily available and abundant materials, be high yielding and tolerant of a wide substrate scope.This work is focused on the copper catalyzed one-pot synthesis of N-aryl oxazolidinones from amino alcohols and aryl iodides. An in situ cyclization of amino alcohol carbamates, followed by a copper catalyzed Ullmann cross-coupling is performed to prepare the corresponding N-aryl oxazolidinone in high yields (75-95%), without the need for isolation and purification of the intermediate oxazolidinone. Results have shown substrate selectivity can be achieved through temperature control, as well as exclusive C-I insertion over other competing halides. This methodology was then used to prepare intermediates used in the synthesis of pharmaceutical compounds.In addition, the development of novel catalytic processes for the functionalization and rearrangement of the oxazolidinone core has also been achieved to prepare new ligands and directing groups for organic synthesis.

Catalytic synthesis and functionalization of <i>N</i>-aryl oxazolidinones

248th National Meeting (2014)

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Catalytic synthesis and functionalization of N-aryl oxazolidinones