Novel lactonization of ethenetricarboxylate derivatives: intermolecular trapping of alkenes.
A novel cyclization of 1,1-diethyl 2-tert-butyl ethenetricarboxylate (1a) in the presence of a Lewis acid afforded a 5,5-dimethyl-gamma-lactone derivative 2a. The reaction process has been shown to arise from formation by trapping of isobutylene generated in situ. Lewis acid-promoted intermolecular reactions of 1,1-diethyl 2-hydrogen ethenetricarboxylate (5) and various alkenes to afford highly functionalized gamma-lactones were also developed. [reaction: see text]
Yamazaki
Shoko
S
Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan. yamazaks@nara-edu.ac.jp
Ohmitsu
Kanae
K
Ohi
Kunihiro
K
Otsubo
Tetsuya
T
Moriyama
Kayo
K
D000475:Alkenes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D007783:Lactones / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000475:Alkenes; D002264:Carboxylic Acids; D007202:Indicators and Reagents; D007783:Lactones