Diastereoselective Approach to Substituted Oxazolidinones from Morita–Baylis–Hillman Adducts

Abstract

We disclose herein a new strategy for the diastereoselective preparation of 4- and 4,5-substituted oxazolidinones from Morita–Baylis–Hillman adducts. The strategy is based on an intramolecular cyclization involving a nucleophilic attack of an alkoxide ion to the carbonyl group of a carbamate. The latter is prepared from a Curtius rearrangement having Morita–Baylis–Hillman adduct as substrate. The oxazolidinones were prepared in six steps with an overall yield of 18% and 49%.

Keywords:

• Curtius rearrangement
• heterocycles
• Morita–Baylis–Hillman
• oxazolidinones

ACKNOWLEDGMENTS

P. R. and P. H. S. P. thank FAPESP for fellowships. F. C. thanks FAPESP for financial support and CNPq for financial support and a research fellowship.