title: Inherently chiral iminoresorcinarenes through regioselective unidirectional tautomerization.
abstract: Tetraformylresorcin[4]arene is obtained in 48% yield via a chromatography-free Duff reaction. The formylated resorcinarene reacts easily with primary aliphatic and aromatic amines. The resulting imines exist exclusively in keto-enamine forms. Owing to a system of intramolecular hydrogen bonds, the reaction selectively leads to regioisomers with C4 symmetry. They possess an inherent chirality due to a propeller-like skeleton. For chiral amines, inherently chiral diastereoisomers are observed.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Marcin
authors.initials: M
authors.lastname: Grajda
authors.forename: Michał
authors.initials: M
authors.lastname: Wierzbicki
authors.forename: Piotr
authors.initials: P
authors.lastname: Cmoch
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Szumna