Catalytic asymmetric epoxidation of α,β-unsaturated phosphane oxides with a Y(O-iPr)3/biphenyldiol complex

被引:30
作者
Hara, Keiichi [1 ]
Park, So-Young [1 ]
Yamagiwa, Noriyuki [1 ]
Matsunaga, Shigeki [1 ]
Shibasaki, Masakatsu [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
asymmetric catalysis; biaryldiols; epoxidation; organophosphorus compounds; yttrium;
D O I
10.1002/asia.200800035
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:1500 / 1504
页数:5
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