Asymmetric allylation of unsymmetrical 1,3-diketones using a BINAP-palladium catalyst.
[reaction: see text] The chiral palladium complex generated in situ from [Pd(eta(3)-allyl)Cl](2) and (R)-BINAP is a good catalyst for the catalytic asymmetric allylation of 1,3-diketones. The reaction provided chiral 2,2-dialkyl-1,3-diketones with 64-89% ee in high yields (13 examples). Enantiomeric excesses are strongly affected by the gamma-substituent of the allylic substrates. A variety of unsymmetrical 1,3-diketones were alkylated with cinnamyl acetate in good enantioselectivities via use of the BINAP-palladium catalyst (77-89% ee).
Kuwano
Ryoichi
R
Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan. rkuwascc@mbox.nc.kyushu-u.ac.jp
Uchida
Kei-Ichi
K
Ito
Yoshihiko
Y