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Diels–Alder Reactions of 2-Vinylindoles with Open-Chain C=C Dienophiles

✍ Scribed by Giorgio Abbiati; Valentina Canevari; Diego Facoetti; Elisabetta Rossi

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
194 KB
Volume
2007
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

The synthesis of diastereoisomeric 3,4‐disubstituted 1,2,3,4‐tetrahydrocarbazoles by Diels–Alder cycloaddition reactions between [(E)‐2‐vinyl]indole‐1‐carboxylic acid ethyl esters and open‐chain C=C dienophiles is reported and discussed. The reactions proceed with high regioselectivity whereas the diastereoselectivity ranges from moderate to excellent depending on the substitution pattern on both the dienes and dienophiles and on the catalyst employed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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