One-pot Synthesis of Chiral <i>cis</i>-Hydrindanes via Diphenylprolinol Silyl Ether Mediated Domino Reaction and Aldol Condensation
Nariyoshi Umekubo, Ryohei Iwata, Yujiro Hayashi
Abstract
Substituted chiral hydrindanes were synthesized as single isomers in almost enantiopure forms through a one-pot process that proceeds via the diphenylprolinol silyl ether mediated-domino Michael/Michael reaction of α,β-unsaturated aldehydes and 3-hexene-2,5-dione, and a subsequent intramolecular aldol condensation of the generated cyclopentanone intermediate. Substituted chiral hydrindanes were synthesized as single isomers in almost enantiomerically pure form in a one-pot process via a domino diphenylprolinol silyl ether mediated-Michael/Michael reaction of α,β-unsaturated aldehyde and 3-hexene-2,5-dione, followed by intramolecular aldol condensation of the generated cyclopentanone.
Topics & Concepts
ChemistryCyclopentanoneMichael reactionAldol condensationAldol reactionDominoEnantiopure drugIntramolecular forceOrganic chemistryAldehydeSilylationEnantioselective synthesisCatalysisAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions