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

Abstract Topologically unique chiral noradamantanes are 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 are formed, and six chiral centers, including one all‐carbon quaternary center, are generated, five of which are fully controlled. These functionalized noradamantanes are 3D, cage‐like molecules that can serve as valuable chiral building blocks for drug design.