Chemistry of 4-trimethylsilyl-3-dialkylaminocrotonate esters and the cycloaromatization reactions with enamines
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 compounds in a 4C+2C combination.A mechanism for this cycloaromatization reaction is proposed.
Kang, G. J.,Chan, T. H.
p. 3102 - 3110
(2007/10/02)
Unexpected Regiochemistry in the Reaction of some γ-Trimethylsilylated 3-Dialkylamino-crotonate Esters with Carbonyl Electrophiles.
4-Trimethylsilyl-3-dialkylaminocrotonate esters (4) react with a number of carbonyl electrophiles and titanium tetrachloride to give products with substitution at γ-position.A dynamic equilibrium of 4 and its O-silyl isomer 16 is proposed to explain the regiochemistry.
Chan, T.H.,Kang, G.J.
p. 3011 - 3014
(2007/10/02)
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