Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine.
[reaction: see text]. Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins proceeded with high enantioselectivity in the presence of a rhodium catalyst (3 mol %) generated from Rh(acac)(C2H4)2 and (R)-Segphos to give the corresponding (R)-4-arylchroman-2-ones in over 99% ee. This asymmetric reaction was applied to the synthesis of (R)-tolterodine.
Chen
Gang
G
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Tokunaga
Norihito
N
Hayashi
Tamio
T
D001559:Benzhydryl Compounds / Q000032:analysis / Q000138:chemical synthesis*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003374:Coumarins / Q000737:chemistry*; D003408:Cresols / Q000032:analysis / Q000138:chemical synthesis*; D015394:Molecular Structure; D010665:Phenylpropanolamine / Q000032:analysis / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D000068737:Tolterodine Tartrate
D001559:Benzhydryl Compounds; D001897:Boronic Acids; D003374:Coumarins; D003408:Cresols; D010665:Phenylpropanolamine; D000068737:Tolterodine Tartrate; D012238:Rhodium