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

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.