Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene-Imine [3 + 2] Annulation

We have prepared a previously unreported family of P-stereogenic [2.2.1] bicyclic chiral phosphines through straightforward syntheses starting from the natural product carvone. This design rationale prompted the development of an unforeseen C-dealkenylation reaction. We have applied these organocatalysts in the asymmetric syntheses of a bevy of pyrrolines, obtained in high yields and enantioselectivities, including a biologically active small molecule, efsevin.