An organocatalytic oxidative coupling strategy for the direct synthesis of arylated quaternary stereogenic centers.
A broadly applicable oxidative coupling strategy of 3-substituted catechols and carbon-centered pro-nucleophiles for the construction of arylated quaternary stereogenic centers has been developed. Pivoting on a base-catalyzed addition of a carbon-centered acid to an in situ generated o-benzoquinone, the method is general and atom-economical and provides remarkably efficient access to one of the most challenging structural motifs. Furthermore, use of chiral bifunctional organocatalysts allows the process to be rendered asymmetric (up to 81% ee).
Bogle
Katherine M
KM
School of Chemistry, The University of Manchester, Oxford Road, Manchester, UK.
Hirst
David J
DJ
Dixon
Darren J
DJ
D016227:Benzoquinones / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry; D002384:Catalysis; D002396:Catechols / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D009930:Organic Chemicals / Q000737:chemistry*; D010084:Oxidation-Reduction; D010648:Phenylacetates / Q000737:chemistry; D013237:Stereoisomerism
D016227:Benzoquinones; D001688:Biological Products; D002396:Catechols; D009930:Organic Chemicals; D010648:Phenylacetates; C004532:quinone; C034221:catechol; C521816:ethyl phenylacetate