Titanium (IV) chloride, zirconium (IV) chloride or boron trichloride and phosphine-promoted Baylis–Hillman reaction of aldehydes with α, β-unsaturated ketone

M Shi, JK Jiang, SC Cui, YS Feng

Index: Shi, Min; Jiang, Jian-Kang; Cui, Shi-Cong; Feng, Yan-Shu Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 4 p. 390 - 393

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Abstract

In the Baylis–Hillman reaction of aldehydes with an α, β-unsaturated ketone, the chlorinated compound 1 was obtained as the major product using tributylphosphine as a Lewis base in the presence of titanium (IV) chloride, zirconium (IV) chloride or boron trichloride in dichloromethane at<− 20° C. A plausible reaction mechanism has been proposed. Using (R)- (+)-2, 2′-bis (diphenylphosphino)-1, 1′-binaphthyl (BINAP) as a chiral Lewis base, 10% ...