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

作者：Rezende Patricia; Paioti Paulo H S; Coelho Fernando^*

来源：Synthetic Communications, 2011, 41(2): 227-242.

DOI：10.1080/00397910903534023

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

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%.

• 出版日期2011