Diastereoselective syntheses of pyrazolyl isoxazolidines via 1,3-dipolar cycloaddition |
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| Authors: | Kesavan Karthikeyan Sundaresan Etti |
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| Institution: | a Organic Chemistry Division, Central Leather Research Institute, Sardar Patel Road, Adyar, Chennai-600020, Tamil Nadu, India
b Centre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai-600025, Tamil Nadu, India |
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| Abstract: | Synthesis of novel 2,3,4,5-tetrasubstituted isoxazolidine and 2,3,5-trisubstituted isoxazolidine by 1,3-dipolar cycloaddition of nitrones with electron-deficient and electron-rich olefins is described. 1,3-Dipolar cycloaddition of nitrones with β-nitrostyrene, gives exclusively endo-diastereoisomer of isoxazolidine and with ethyl vinyl ether, gives exo-diastereoisomer of isoxazolidine with de >95%. The stereochemistry of the products were assigned using extensive NMR studies. |
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