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http://dx.doi.org/10.5012/bkcs.2010.31.6.1515

Regio- and Diastereoselective 1,3-Dipolar Cycloaddition between Perfluoro-2-methyl-2-pentene and Nitrones: A Facile Approach to Partially-Fluorinated Isoxazolidines  

Moon, Mi-Eun (Department of Chemistry, University of Ulsan)
Park, Joo-Yeon (Department of Chemistry, University of Ulsan)
Jeong, Eun-Ha (Department of Chemistry, University of Ulsan)
Vajpayee, Vaishali (Department of Chemistry, University of Ulsan)
Kim, Hyun-Uk (Department of Chemistry, POSTECH)
Chi, Ki-Whan (Department of Chemistry, University of Ulsan)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.6, 2010 , pp. 1515-1518 More about this Journal
Abstract
Regio- and diastereoselective 1,3-dipolar cycloaddition reactions of nitrones {(Z)-${\alpha}$-phenyl-N-methylnitrone (1a) and (Z)-${\alpha}$-propyl-N-butylnitrone (1b)} with electron-deficient perfluoro-2-methyl-2-pentene (2) lead to novel isoxazolidines {5-fluoro-5-pentafluoroethyl-4,4-bis-trifluoromethyl-2-methyl-3-phenyl-isoxazolidine (3a) and 2-butyl-5-fluoro-5-pentafluoroethyl-4,4-bis-trifluoromethyl-3-propyl-isoxazolidines (3b) respectively} as major constituents. These derivatives were characterized by IR, $^1H$ and $^{19}F$ NMR, GC-MS and NOE measurements, and the absolute structure of 3a was confirmed by X-ray crystallography.
Keywords
Perfluorinated olefin; 1,3-Dipolar cycloaddition; Isoxazolidine derivatives;
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