Catalytic asymmetric epoxidation of alpha,beta-unsaturated phosphane oxides with a Y(O-iPr)3/biphenyldiol complex.
A rare-earth-metal-catalyzed asymmetric epoxidation of alpha,beta-unsaturated phosphane oxides is described. The appropriate selection of a chiral ligand and an achiral additive is important for achieving good reactivity and enantioselectivity. A Y(O-iPr)(3)/biphenyldiol complex with an achiral phosphane oxide additive afforded beta-aryl alpha,beta-epoxy phosphane oxides in 77-99 % yield and with 96-98 % ee. With beta-alkyl substrates, the reaction proceeded smoothly in the absence of an achiral additive, and beta-alkyl alpha,beta-epoxy phosphane oxides were obtained in 94-99 % yield and with 87-95 % ee.
Hara
Keiichi
K
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Japan.
Park
So-Young
SY
Yamagiwa
Noriyuki
N
Matsunaga
Shigeki
S
Shibasaki
Masakatsu
M
D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism; D015019:Yttrium / Q000737:chemistry*
D004852:Epoxy Compounds; D010087:Oxides; D010636:Phenols; D010720:Phosphines; D015019:Yttrium; C044646:phosphine