title: Chiral 2 + 3 Keto-Enamine Pseudocyclophanes Derived from 1,3,5-Triformylphloroglucinol.
abstract: The reactions of 1,3,5-triformylphloroglucinol with (1R,2R)-1,2-diaminocyclohexane, (1R,2R)-1,2-diphenylethylenediamine, or (R)-2,2'-diamino-1,1'-binaphthyl result in the formation of enantiopure [2 + 3] keto-enamine condensation products, in contrast to analogous reactions of 1,3,5-triformylbenzene, where [4 + 6] Schiff base cages are formed. The X-ray crystal structure of the diaminocyclohexane 2 + 3 derivative as well as modeled structures of other compounds of this type show cyclophane-like molecules with close contact between the phloroglucinol rings. Density Functional Theory (DFT) calculations confirm that there is a sizable π-π interaction between these rings influencing the conformation of these molecules.
authors.affiliation: Department of Chemistry, University of Wrocław , 14 F. Joliot-Curie, 50-383 Wrocław, Poland.
authors.forename: Przemysław
authors.initials: P
authors.lastname: Kieryk
authors.affiliation: Institute of Low Temperature and Structure Research, Polish Academy of Sciences , P.O. Box 1410, 50-950, Wrocław, Poland.
authors.forename: Jan
authors.initials: J
authors.lastname: Janczak
authors.affiliation: Department of Chemistry, University of Wrocław , 14 F. Joliot-Curie, 50-383 Wrocław, Poland.
authors.forename: Jarosław
authors.initials: J
authors.lastname: Panek
authors.affiliation: Department of Chemistry, University of Wrocław , 14 F. Joliot-Curie, 50-383 Wrocław, Poland.
authors.forename: Marcin
authors.initials: M
authors.lastname: Miklitz
authors.affiliation: Department of Chemistry, University of Wrocław , 14 F. Joliot-Curie, 50-383 Wrocław, Poland.
authors.forename: Jerzy
authors.initials: J
authors.lastname: Lisowski
mesh_terms: D018360:Crystallography, X-Ray; D003510:Cyclohexanes / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C000607859:1,3,5-triformylphloroglucinol; D003510:Cyclohexanes; D012545:Schiff Bases; D010696:Phloroglucinol