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
Diels-Alder reactions of 2-vinylindoles with open-chain C=C dienophiles / G. Abbiati, V. Canevari, D. Facoetti, E. Rossi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2007:3(2007), pp. 517-525. [10.1002/ejoc.200600625]
Diels-Alder reactions of 2-vinylindoles with open-chain C=C dienophiles
G. AbbiatiPrimo
;V. CanevariSecondo
;D. FacoettiPenultimo
;E. RossiUltimo
2007
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
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