1055424-74-2Relevant academic research and scientific papers
A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization
Canterbury, Daniel P.,Herrick, Ildiko R.,Um, Joann,Houk,Frontier, Alison J.
experimental part, p. 3165 - 3179 (2009/09/05)
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.
Origins of stereoselectivity in the oxido-alkylidenation of alkynes
Canterbury, Daniel P.,Frontier, Alison J.,Um, Joann M.,Cheong, Paul H.-Y.,Goldfeld, Dahlia A.,Huhn, Richard A.,Houk
supporting information; experimental part, p. 4597 - 4600 (2009/05/13)
(Chemical Equation Presented) A mild, convenient oxido-alkylidenation of alkynes is described. The three-step sequence involves the 1,3-dipolar cycloaddition of a nitrone and an alkynoate, oxidation of the resulting isoxazoline, and stereoselective extrusion of nitrosomethane. Quantum mechanical calculations identified the interactions of R3 with the oxidant and the preferred conformation of a diradical intermediate as major factors controlling the stereoselectivity of the oxidation and torquoselectivity of the extrusion.
