Stereoselective synthesis of either (E)-or (Z)-silyl enol ether from the same acyclic α, β-unsaturated ketone using cationic rhodium complex-catalyzed 1, 4- …

…, R Hachisuka, T Noguchi, H Miura, T Hashimoto…

Index: Onodera, Gen; Hachisuka, Ryosuke; Noguchi, Tomomi; Miura, Hiroki; Hashimoto, Toru; Takeuchi, Ryo Tetrahedron Letters, 2014 , vol. 55, # 2 p. 310 - 313

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Abstract

Abstract The stereoselective synthesis of either (E)-or (Z)-silyl enol ether from the same acyclic α, β-unsaturated ketone is reported. Highly (Z)-selective conditions were the use of [Rh (cod) 2] BF 4/DPPE at room temperature with no solvent, whereas (E)-selective conditions were the use of [Rh (cod) 2] BF 4/P (1-Nap) 3 (1-Nap= 1-naphthyl) under refluxing dichloromethane.