Asymmetric Synthesis of Noradamantane Scaffolds via Diphenylprolinol Silyl Ether‐Mediated Domino Michael/Epimerization/Michael (or Aldol)/1,2‐Addition Reactions

Topologically unique chiral noradamantanes were synthesized using a diphenylprolinol silyl ether‐mediated domino Michael/epimerization/Michael/1,2‐addition or Michael/epimerization/aldol/1,2‐addition reaction with excellent enantioselectivity in a single reaction vessel. Three carbon–carbon bonds were formed, and six chiral centers, including one all‐carbon quaternary center, were generated, five of which were fully controlled. These functionalized noradamantanes are three‐dimensional, cage‐like molecules that could serve as valuable chiral building blocks for drug design.