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Paper | Regular issue | Vol 75, No. 6, 2008, pp.1407-1416
Published online, 12th February, 2008
DOI: 10.3987/COM-07-11318
Hf(OTf)4-Catalyzed 1,4-Addition Reactions of Indole to Enone in the Presence of Meso and Chiral Pyridinediamine Ligands

Sachiko Aburatani and Jun’ichi Uenishi*

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan

Abstract

Hf(OTf)4-catalyzed 1,4-addition reactions of indole to enones in the presence of pyridinediamine are described. Although a dimer and a trimer of indole were produced under the Hf(OTf)4 catalyzed reaction conditions of indole, the addition of pyridinediamines (La-f) inhibited such oligomerization reactions. A 1:1 mixture of Hf(OTf)4 and a pyridinediamine ligand formed a Hf(OTf)4- pyridinediamine complex, which catalyzed the 1,4-addition reaction very efficiently without the formation of dimer and trimer of indole. The stereochemistry of the pyridinediamine ligands was found to play an important role in the relative rate of the reactions.