Strictly Regiocontrolled α-Monosubstitution of Cyclic Carbonyl Compounds with Alkynyl and Alkyl Groups via Pd-Catalyzed Coupling of Cyclic α-Iodoenones with …

E Negishi, Z Tan, SY Liou, B Liao

Index: Negishi, Ei-Ichi; Tan, Ze; Liou, Show-Yee; Liao, Baiqiao Tetrahedron, 2000 , vol. 56, # 52 p. 10197 - 10207

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Citation Number: 59

Abstract

The conditions for the Pd-catalyzed cross coupling of cyclic α-iodoenones, such as 2-iodo-2- cyclohexenone, with alkynylzincs have been optimized. The use of tris (o-furyl) phosphine (TFP) as a ligand and DMF as a solvent has led to the formation of α-alkynylenones in excellent yields. This optimized procedure has been applied to the synthesis of (±)- harveynone and (±)-tricholomenyn A in high yields. Investigation of related α-alkylation ...