A Torquoselective Extrusion of Isoxazoline N-Oxides. Application to the Synthesis of Aryl Vinyl and Divinyl Ketones for Nazarov Cyclization.
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.
Canterbury
Daniel P
DP
Department of Chemistry, University of Rochester, Rochester, New York, 14627.
Herrick
Ildiko R
IR
Um
Joann
J
Houk
K N
KN
Frontier
Alison J
AJ