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Lewis Acid Catalyzed [4 + 2] Cycloaddition of N-Tosylhydrazones with ortho-Quinone Methides
Chun-Ying Wang1, Jia-Bin Han1, Long Wang1
1School of Chemistry and Chemical Engineering, Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, Key Laboratory of Material Chemistry for Energy Conversion and Storage , Huazhong University of Science and Technology , 1037 Luoyu Road , Wuhan 430074 , People's Republic of China.
Abstract:
A formal [4 + 2] cycloaddition of N-tosylhydrazones with ortho-quinone methides was developed, affording the facile synthesis of diverse 1,3-oxazine derivatives under mild conditions. In this transformation, N-tosylhydrazones are used as a 1,2-dipole synthon under base-free conditions. Moreover, the substrate scope is broad, and the products are formed with high diastereoselectivities in most of the cases.
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