W. Kim, Eunyoung Yoon, Kyoung A Jo
Aug 20, 2011
Citations
0
Influential Citations
8
Citations
Journal
Bulletin of The Korean Chemical Society
Abstract
Oxazolidinones and their derivatives are widely used, as chiral synthons or chiral auxiliaries and as bioactive scaffolds in numerous natural products. Due to the importance of their structures, several methods for the synthesis of 1,3oxazolidin-2-ones have been reported. Classical methods for formation of these heterocyclic rings involve condensation reactions between corresponding amino alcohols and carbonyl precursors such as phosgene, chloroformate and dialkyl carbonates. An alternative approach is the cyclization reaction of vinyl or propargyl carbamate catalyzed by base or transition metal catalyst, in which a variety of substituted oxazolidinones are obtained under milder conditions. Tamaru, Gagosz, and Schmalz reported the synthesis of 4-alkylidene1,3-oxazolidin-2-one from O-propargyl carbamates using Cu(I) and Au(I) catalyst, whereas Chandrasekaran reported LiOH-catalyzed reaction method with DMF solvent. However, these procedures were mostly applied to the construction of 4-methylene-1,3-oxazolidin-2-one, and only a few 4-substituted methylene ones have been reported. Another method using CO2 as a carbonyl source has also been developed, 5