Asymmetric Synthesis of Noradamantane Scaffolds via Diphenylprolinol Silyl Ether‐Mediated Domino Michael/Epimerization/Michael (or Aldol)/1,2‐Addition Reactions
Abstract
AbstractTopologically 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.
Article Details
Authors (7)
Konstantinos Daskalakis
Department of Chemistry Graduate School of Science Tohoku University 6‐3 Aramaki Aza‐Aoba, Aoba‐ku Sendai Miyagi 980–8578 Japan
Nariyoshi Umekubo
Department of Chemistry Graduate School of Science Tohoku University 6‐3 Aramaki Aza‐Aoba, Aoba‐ku Sendai Miyagi 980–8578 Japan
Satrajit Indu
Department of Chemistry Graduate School of Science Tohoku University 6‐3 Aramaki Aza‐Aoba, Aoba‐ku Sendai Miyagi 980–8578 Japan
Genki Kawauchi
Department of Chemistry Graduate School of Science Tohoku University 6‐3 Aramaki Aza‐Aoba, Aoba‐ku Sendai Miyagi 980–8578 Japan
Tohru Taniguchi
Frontier Research Center for Advanced Material and Life Science, Faculty of Advanced Life Science, Hokkaido University, North 21 West 11, Sapporo 001-0021, Japan
Kenji Monde
Yujiro Hayashi