Preparation of 3-acetyl-2-hydroxyindoles via rhodium carbenoid aromatic carbon-hydrogen insertion

N Etkin, SD Babu, CJ Fooks, T Durst

Index: Etkin, Nola; Babu, Suresh D.; Fooks, Catherine J.; Durst, Tony Journal of Organic Chemistry, 1990 , vol. 55, # 3 p. 1093 - 1096

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Citation Number: 56

Abstract

Diethyl (IS, SR)-[1'Phenyl-2'-(p-tolylsulfinyl) ethyl]-malonate (23) and (IR, SR)-24. To a solution of diethyl malonate (190 mg, 1.2 mmol) in THF (0.5 mL) at-78" C under nitrogen was added du L i (0.49 mL, 0.78 mol, 1.6 M in hexane). The mixture was warmed to room temperature, and 20C (100 mg, 0.4 mmol) in THF (0.5 mL) was added. The solution was refluxed for 6.5 days and then cooled to room temperature. CHzClz (50 mL) was then ...