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Diels–Alder Reactions of 2‐Vinylindoles with Open‐Chain C=C Dienophiles
Author(s) -
Abbiati Giorgio,
Canevari Valentina,
Facoetti Diego,
Rossi Elisabetta
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600625
Subject(s) - chemistry , regioselectivity , cycloaddition , indole test , diels–alder reaction , catalysis , organic chemistry , medicinal chemistry
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)