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. 2003 Jun 12;5(12):2177-9.
doi: 10.1021/ol034665s.

Asymmetric allylation of unsymmetrical 1,3-diketones using a BINAP-palladium catalyst

Ryoichi Kuwano  1 , Kei-Ichi Uchida, Yoshihiko Ito
Affiliations

Asymmetric allylation of unsymmetrical 1,3-diketones using a BINAP-palladium catalyst

Ryoichi Kuwano et al. Org Lett. .

Abstract

[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).

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