Organic letters

Regiocontrolled Synthesis of Carbocycle-Fused Indoles via Arylation of Silyl Enol Ethers with o-Nitrophenylphenyliodonium Fluoride

T Iwama, VB Birman, SA Kozmin, VH Rawal

Index: Iwama, Tetsuo; Birman, Vladimir B.; Kozmin, Sergey A.; Rawal, Viresh H. Organic Letters, 1999 , vol. 1, # 4 p. 673 - 676

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Citation Number: 77

Abstract

A new, regiocontrolled synthesis of carbocycle-fused indoles has been developed. The two- step procedure involves first the regiospecific arylation of silyl enol ethers with o- nitrophenylphenyliodonium fluoride (1). Reduction of the nitro group on the aromatic ring with TiCl3 followed by spontaneous condensation of the aniline with the ketone then affords the indole products.

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