A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization

Daniel P Canterbury,Ildiko R Herrick,Joann Um,K.N Houk,Alison J Frontier

doi:10.1016/j.tet.2008.10.003

A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization

Daniel P Canterbury, Ildiko R Herrick + Show 3 more

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https://doi.org/10.1016/j.tet.2008.10.003

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Journal: Tetrahedron	Publication Date: Oct 10, 2008
Citations: 30

Affiliation: University of Rochester, University of California, Los Angeles

#Aryl Vinyl Ketones #Divinyl Ketones + Show 8 more

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Abstract

A mild, convenient reaction sequence for the synthesis of Nazarov cyclization substrates is described. The [3+2] dipolar cycloaddition of a nitrone and an electron-deficient alkyne gives an isolable isoxazoline intermediate, which upon oxidation undergoes stereoselective extrusion of nitrosomethane to give aryl vinyl or divinyl ketones.

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