Canadian journal of chemistry

Chemistry of 4-trimethylsilyl-3-dialkylaminocrotonate esters and the cycloaromatization reactions with enamines

GJ Kang, TH Chan

Index: Kang, G. J.; Chan, T. H. Canadian Journal of Chemistry, 1985 , vol. 63, p. 3102 - 3110

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Citation Number: 9

Abstract

Methyl 4-trimethylsilyl-3-dialkylaminocrotonate is synthesized by the silylation of methyl 3- dialkylaminocrotonate. It reacts with carbonyl electrophiles at its γ-position. The unusual regiochemistry of this reaction is studied and rationalized. It reacts with enamines derived from acyclic ketones to give aromatic compounds in a 3C+ 3C combination and with enamines derived from cycloketones of 5-to 8-membered rings to give aromatic ...

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