Rhodium-catalyzed asymmetric arylation of β,γ-unsaturated α-ketoamides for the construction of nonracemic γ,γ-diarylcarbonyl compounds.
A highly regio- and enantioselective rhodium-catalyzed 1,4-addition of arylboronic acids to β,γ-unsaturated α-ketoamides using a simple new chiral sulfinylphosphine ligand is described. This transformation provides an attractive approach to construct chiral nonracemic γ,γ-diarylsubstituted carbonyl compounds, as exemplified in the concise syntheses of sertraline and tetrahydroquinoline-2-carboxylamide.
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (China); University of Chinese Academy of Sciences, Beijing 100049 (China); Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (China).
Juanjuan
J
Wang
Min
M
Wang
Peng
P
Cao
Liyin
L
Jiang
Guihua
G
Chen
Jian
J
Liao
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D008024:Ligands; D010720:Phosphines / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D001897:Boronic Acids; D008024:Ligands; D010720:Phosphines; D012238:Rhodium; C044646:phosphine
S,P ligands; asymmetric synthesis; enantioselectivity; homogeneous catalysis; rhodium