title: Reductive coupling of phthalimides with ketones and aldehydes by low-valent titanium: one-pot synthesis of alkylideneisoindolin-1-ones.
abstract: The reductive coupling of phthalimides with ketones and aldehydes by Zn-TiCl4 in THF gave two- and four-electron reduced products, 3-hydroxy-3-(1-hydroxyalkyl)isoindolin-1-ones and alkylideneisoindolin-1-ones, selectively by controlling the reaction conditions. Therefore, the one-pot synthesis of alkylideneisoindolin-1-ones from phthalimides was effected by this reaction. Although the alkylideneisoindolin-1-ones prepared from phthalimides and aldehydes were formed as mixtures of geometric isomers in most cases, the geometric ratios could be increased by reflux in cat. PPTS/toluene. After the isomerization, the E-isomers of N-methyl substituted alkylideneisoindolin-1-ones (X = Me, R(1) = R, R(2) = H) and the Z-isomers of N-unsubstituted alkylideneisoindolin-1-ones (X = H, R(1) = H, R(2) = R) were obtained preferentially.
authors.affiliation: Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University ,4-101, Koyama-cho Minami, Tottori 680-8552, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Kise
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kawano
authors.forename: Toshihiko
authors.initials: T
authors.lastname: Sakurai