To form biologically active and chemically useful isoxazolines, nitrile oxides have been reported to react with alkenes.  These types of reactions typically involve toxic solvents and/or reagents.  In the interest of making organic reactions more environmentally benign, we are currently developing a greener path to the formation of isoxazolines.  We have demonstrated that nitrile oxides undergo 1,3-dipolar cycloaddition with alkenes in aqueous organized media to form the subsequent isoxazolines.  Further, we have demonstrated that oximes, common nitrile oxide precursors, can be formed from aldehydes under the same reaction conditions.  Thus, both steps can be successfully combined to generate isoxazolines in a single pot from aldehydes.

Development of a green single pot synthesis of isoxazolines via 1,3-dipolar cycloaddition of nitrile oxides

243rd National Meeting (2012)

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