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

Ryoichi Kuwano; Kei Ichi Uchida; Yoshihiko Ito

doi:10.1021/ol034665s

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

Ryoichi Kuwano, Kei Ichi Uchida, Yoshihiko Ito

Multidisciplinary chemistry

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

(Matrix presented) The chiral palladium complex generated in situ from [Pd(η³-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 γ-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).

Original language	English
Pages (from-to)	2177-2179
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	12
DOIs	https://doi.org/10.1021/ol034665s
Publication status	Published - Jun 12 2003

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

abstract = "(Matrix presented) The chiral palladium complex generated in situ from [Pd(η3-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 γ-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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T1 - Asymmetric allylation of unsymmetrical 1,3-diketones using a BINAP-palladium catalyst

AU - Kuwano, Ryoichi

AU - Uchida, Kei Ichi

AU - Ito, Yoshihiko

PY - 2003/6/12

Y1 - 2003/6/12

N2 - (Matrix presented) The chiral palladium complex generated in situ from [Pd(η3-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 γ-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).

AB - (Matrix presented) The chiral palladium complex generated in situ from [Pd(η3-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 γ-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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Asymmetric allylation of unsymmetrical 1,3-diketones using a BINAP-palladium catalyst

Abstract

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