Alkyne Cycloadditions Mediated by Tetrabutylammonium Fluoride: A Unified and Diversifiable Route to Isoxazolines and Pyrazolines.

A versatile approach to isoxazolines and pyrazolines by the cyclization of alkyne substrates using tetrabutylammonium fluoride (TBAF) is described. The reported diheteroatom cycles were produced under mild reaction conditions and with broad product scope. Evidence is also provided for a vinyl anion intermediate produced under unusually mild conditions, which was trapped in situ as part of a tandem cyclization/aldehyde addition sequence. Finally, a deprotection/functionalization method is described, leading to a substituted pyrazoline in good diastereoselectivity.