Enantioselective Synthesis of Cyclohexenones

Significance

Based on their previous research (Angew. Chem. Int. Ed. 2008, 47, 7652) and work of Alexakis (Org. Lett. 2004, 6, 3529) in the field of iridium-catalyzed asymmetric allylic substitutions using phosphoramidite ligands, the authors developed a modular sequence for the preparation of chiral cyclohexenones. The target compounds of type 6 were prepared in good overall yields of 34-53% (over five steps) starting from 2. Furthermore, the usability of this concept has been demonstrated in the total synthesis of two natural products, (+)-cryptocaryone and (+)-infectocaryone.