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ChemInform Abstract: The Ultra High Pressure Conjugate Addition of Indoles to Electron-Deficient Olefins.

✍ Scribed by Paul Harrington; Michael A. Kerr

Publisher
John Wiley and Sons
Year
2010
Weight
38 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

The Ultra High Pressure Conjugate Addition of Indoles to Electron-Deficient Olefins. -Indole and methylindole are added to Ξ±,Ξ²-unsaturated ketones in the presence of catalytic amounts of Yb(OTf) 3 to afford 3-alkylated indoles. The more reactive and less sterically hindered electrophiles give good to excellent yields of expected products, whereas the reaction with sterically hindered enones proceeds at high pressure (13 kbar) with remarkable reduction of the reaction time and with increased yields. Even extremely hindered cyclic enones (VIII) and (Xb), and acrylate (XII) at high pressure produce small amounts of isolable products. -(HARRINGTON,

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