Sweeney, Joseph B. and Sançon, Julien (2008) A Low-Temperature Ammonium Ylid Rearrangement: Enhanced Reactivity Engendered by Rigidity. Synlett, 2008 (14). pp. 2213-2214. ISSN 0936-5214

Sigmatropic rearrangement of tetrahydropyridine-­derived ammonium is a valuable method for the preparation of substituted prolines. These reaction normally require elevated temperatures to proceed, but bicyclic tetrahydropyridine-like ylid 1 undergoes rearrangement at -15 ˚C; the extra rigidity of the azabicyclo[3.3.0]octene system preorganizes the transition state and lowers the activation energy for rearrangement.

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