Organocatalytic atroposelective aldol condensation: synthesis of axially chiral biaryls by arene formation.
Axially chiral compounds are of significant importance in modern synthetic chemistry and particularly valuable in drug discovery and development. Nonetheless, current approaches for the preparation of pure atropisomers often prove tedious. We demonstrate here a synthetic method that efficiently transfers the stereochemical information of a secondary amine organocatalyst into the axial chirality of tri-ortho-substituted biaryls. An aromatic ring is formed during the dehydration step of the described aldol condensation cascade, leading to highly enantioenriched binaphthyl derivatives. The fundamental course of the reaction is related to the biosynthesis of aromatic polyketides.
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel (Switzerland) http://www.chemie.unibas.ch/∼sparr.
Achim
A
Link
Christof
C
Sparr
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000588:Amines; D009281:Naphthalenes; D061065:Polyketides; C116609:3-hydroxybutanal
aldol reaction; atropisomerism; enantioselectivity; organocatalysis; polyketides