Silicon-controlled allylation of 1, 3-dioxo compounds by use of allyltrimethylsilane and ceric ammonium nitrate

JR Hwu, CN Chen, SS Shiao

Index: Hwu, Jih Ru; Chen, Chung Nan; Shiao, Shui-Sheng Journal of Organic Chemistry, 1995 , vol. 60, # 4 p. 856 - 862

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Citation Number: 58

Abstract

Allyltrimethylsilane and CAN. We treated a methanol solution containing a 1, 3-diketone (ie, 10 and 12) and allyltrimethylsilane (5, 1.3 equiv) in methanol with CAN (2.1 equiv). After I 1 min at room temperature, the solution turned from dark brown to pale yellow or colorless. Change of the color indicated completion of the reactions. Workup followed by purification afforded the allylated product &e., 11 and 13) in excellent yields (91-98%; entries 2 and 3 ...