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Review | Regular issue | Vol 78, No. 4, 2009, pp.843-871
Published online, 20th November, 2008
DOI: 10.3987/REV-08-645
Efficient Synthesis of Indoles and Benzo[b]furans via [3,3]-Sigmatropic Rearrangement of N-Trifluoroacetylenehydrazines and Enehydroxylamines

Okiko Miyata,* Norihiko Takeda, and Takeaki Naito*

*Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan

Abstract

This review summarizes an efficient synthesis of benzo[b]furans and indoles via [3,3]-sigmatropic rearrangements of N-trifluoroacetyl enehydroxylamines and enehydrazines, which were triggered by acylation of oxime ethers and hydrazines. TFAA and TFAT-DMAP have been proved to be the best reagent to induce [3,3]-sigmatropic rearrangement for the synthesis of benzo[b]furans and indoles. This method was successfully applied to the short synthesis of natural products.