83577-49-5

Upstream product

• 83577-47-3 methyl 4-(trimethylsilyl)-3-pyrrolidinocrotonate 
• 762-42-5 dimethyl acetylenedicarboxylate 

Relevant academic research and scientific papers

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.

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.