1055424-77-5Relevant academic research and scientific papers
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.
