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

作者：Moon Mi Eun; Park Joo Yeon; Jeong Eun Ha; Vajpayee Vaishali; Kim Hyunuk; Chi Ki Whan^*

来源：Bulletin of the Korean Chemical Society, 2010, 31(6): 1515-1518.

DOI：10.5012/bkcs.2010.31.6.1515

• Perfluorinated olefin
• 1,3-Dipolar cycloaddition
• Isoxazolidine derivatives

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, (1)H and (19)F NMR, GC-MS and NOE measurements, and the absolute structure of 3a was confirmed by X-ray crystallography.

• 出版日期2010-6-20