title: A novel[2 + 3]cycloaddition reaction: singlet oxygen mediated formation of 1,3-dipole from iminodiacetic acid dimethyl ester and its addition to maleimides.
abstract: Sensitized photolysis of iminodiacetic acid methyl ester and maleimides follows a [2 + 3] cycloaddition pathway yielding pyrrolidine derivatives. This is similar to the photochemical reaction between C(60) and amines. A series of pyrrolidine derivatives are prepared by the method including multipyrrolidines from bis- and tris-maleimide starting materials. The yields range from 13% to 85%. The reaction is highly stereoselective. All the isolated products have the 1,3-dimethoxycarbonyl groups in the cis configuration. Various sensitizers may be used with slightly different yields. A plausible mechanism is proposed that involves the singlet oxygen abstraction of two alpha hydrogen atoms from the iminodiacetate and formation of a 1,3-dipole with a structure similar to the classical thermally generated 1,3-dipole.
authors.affiliation: State Key Laboratory of Rare Earth Materials Chemistry and Applications, Department of Chemistry, Peking University, Beijing 100871, China.
authors.forename: H
authors.initials: H
authors.lastname: Cheng
authors.forename: L
authors.initials: L
authors.lastname: Gan
authors.forename: Y
authors.initials: Y
authors.lastname: Shi
authors.forename: X
authors.initials: X
authors.lastname: Wei