Enantioselective Synthesis of Chromanones via a Peptidic Phosphane Catalyzed Rauhut-Currier Reaction.
The enantioselective intramolecular Rauhut-Currier reaction has been developed using a bifunctional dipeptidic phosphane catalyst, providing a direct access to biologically active α-methylene-δ-valerolactones in high yields and enantiomeric excesses. The novel catalyst is accessible in only four steps from commercial sources and exhibits unusual binding selectivities for a small molecule, suggesting the possibility for long-range interactions between the catalyst and the substrate.
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom.
Robert J H
RJ
Scanes
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom.
Oleg
O
Grossmann
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom.
André
A
Grossmann
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom.
David R
DR
Spring
D002384:Catalysis; D047188:Chalcones / Q000737:chemistry; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry; D004151:Dipeptides / Q000737:chemistry*; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
D047188:Chalcones; D002867:Chromones; D004151:Dipeptides; D010720:Phosphines; C044646:phosphine