Diastereoselective synthesis of 2,3,4,5-tetrasubstituted isoxazolidines via 1,3-dipolar cycloaddition |
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| Authors: | Vellaisamy Sridharan Shanmugaperumal Sivasubramanian |
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| Institution: | a Department of Organic Chemistry, Madurai Kamaraj University, Palkalai Nagar, Madurai 625 021, India
b Department of Chemistry, Ludwig-Maximilians-University, Butenandt Street 5-13, D-81377 Munich, Germany |
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| Abstract: | The 1,3-dipolar cycloaddition reactions of α-2-methoxyaryl nitrones with nitrostyrenes and chalcones have been investigated. The regiochemistry and stereochemistry of the resultant cycloadducts have been determined with the help of NMR spectroscopy and X-ray analysis. β-Nitrostyrenes add to nitrones to give two geometrical isomers, while the β-methyl-β-nitrostyrene gives a single isomer in relatively low yield. The chalcones give a single cycloadduct upon 1,3-dipolar addition. |
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| Keywords: | 1 3-Dipolar cycloaddition α-2-Methoxyaryl nitrones Stereoselectivity NMR and X-ray analysis |
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