Selective Synthesis of 5‐Substituted N‐Aryloxazolidinones by Cycloaddition Reaction of Epoxides with Arylcarbamates Catalyzed by the Ionic Liquid BmimOAc. Issue 21 (27th June 2016)

• Record Type: Journal Article
• Authors: Elageed, Elnazeer H. M.; Chen, Bihua; Wang, Binshen; Zhang, Yongya; Wu, Shi; Liu, Xiuli; Gao, Guohua
• Is Part Of: European journal of organic chemistry. Issue 21(2016)
• Page Start: 3650
• Page End: 3656
• Publication Date: 2016-06-27
• Subjects: Homogeneous catalysis -- Reaction mechanisms -- Cycloaddition -- Ionic liquids -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600474
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A selective procedure for the synthesis of 5‐substituted N ‐aryloxazolidinones by the coupling of epoxides with arylcarbamates catalyzed by ionic liquids has been developed. The effects of reaction time, reactant molar ratio, amount of catalyst, and temperature were investigated. Under the optimal reaction conditions, BmimOAc exhibited efficient catalytic activity compared with other ionic liquids leading to the formation of 5‐substituted N ‐aryloxazolidinones in excellent yields. In addition, chiral 5‐substituted oxazolidinones were synthesized by this procedure in good‐to‐excellent yields with enantiomeric excesses in excess of 99.9 % starting from chiral terminal epoxides. A possible reaction mechanism is discussed in accord with the results obtained by 1 H NMR spectroscopy and DFT calculations, which indicate the cooperative activation by BmimOAc through the formation of hydrogen bonds with the substrates. Abstract : 5‐Substituted N ‐aryloxazolidinones have been selectively synthesized by the coupling of epoxides with arylcarbamates catalyzed by ionic liquids. Under the optimal conditions, BmimOAc catalyzed the formation of 5‐substituted N ‐aryloxazolidinones in excellent yields. 1 H NMR spectroscopy and DFT calculations indicate the cooperative activation of the substrates by BmimOAc through hydrogen bonding.