cheminform abstract: 1,3-dipolar cycloaddition of n-substituted dipolarophiles and nitrones: highly...

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2008 Isoxazole derivatives R 0240 1,3-Dipolar Cycloaddition of N-Substituted Dipolarophiles and Nitrones: Highly Efficient Solvent-Free Reaction. — Coupling of N-vinylamides of type (III)/(XI)/ (XV) with nitrones under solvent-free conditions offers an efficient approach to isoxa- zoles. Steric effects play an important role. Cycloaddition of the chiral nitrone (XIII) proceeds with high stereoselectivity, while starting from chiral N-vinylamides low stereoselectivity is observed. The products are important building blocks which can smoothly be converted into unsymmetrical aspartate derivatives like (X) and (XXI). — (NGUYEN, T. B.; MARTEL, A.; DHAL*, R.; DUJARDIN, G.; J. Org. Chem. 73 (2008) 7, 2621-2632; CNRS, Univ. Maine, F-72085 Le Mans, Fr.; Eng.) — Jannicke 33- 138

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Page 1: ChemInform Abstract: 1,3-Dipolar Cycloaddition of N-Substituted Dipolarophiles and Nitrones: Highly Efficient Solvent-Free Reaction

2008

Isoxazole derivativesR 0240 1,3-Dipolar Cycloaddition of N-Substituted Dipolarophiles and Nitrones: Highly

Efficient Solvent-Free Reaction. — Coupling of N-vinylamides of type (III)/(XI)/(XV) with nitrones under solvent-free conditions offers an efficient approach to isoxa-zoles. Steric effects play an important role. Cycloaddition of the chiral nitrone (XIII) proceeds with high stereoselectivity, while starting from chiral N-vinylamides low stereoselectivity is observed. The products are important building blocks which can smoothly be converted into unsymmetrical aspartate derivatives like (X) and (XXI). — (NGUYEN, T. B.; MARTEL, A.; DHAL*, R.; DUJARDIN, G.; J. Org. Chem. 73 (2008) 7, 2621-2632; CNRS, Univ. Maine, F-72085 Le Mans, Fr.; Eng.) — Jannicke

33- 138

Page 2: ChemInform Abstract: 1,3-Dipolar Cycloaddition of N-Substituted Dipolarophiles and Nitrones: Highly Efficient Solvent-Free Reaction

2008

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