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Pure Appl. Chem., 2001, Vol. 73, No. 2, pp. 247-250

Effect of ligands on the divalent palladium- catalyzed carbon-carbon coupling reactions. Highly enantioselective synthesis of optically active g-butyrolactones

Xiyan Lu* and Qinghai Zhang

Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China

Abstract: In the palladium (II) -catalyzed enyne coupling reactions, the nitrogen-containing ligand plays the same role as the halide ion to inhibit the β-hydride elimination. Employing the pymox or bisoxazoline as ligands, the catalytic asymmetric cyclization of (Z) -4'-acetoxy-2'-butenyl 2-alkynoates initiated by acetoxypalladation was established with high efficiency (up to 92% ee) to afford the optically active γ-butyrolactones.