title: One-shot preparation of an inherently chiral trifunctional calix[4]arene from an easily available cone-triformylcalix[4]arene.
abstract: Via selective 1,3-distal intramolecular Cannizzaro disproportionation of an easily available cone-triformylcalix[4]arene, an inherently chiral trifunctional cone-calix[4]arene derivative has been prepared. The presence of three different functional groups (-CH2OH, -CHO and -COOH) at the upper rim of the calixarene scaffold makes this compound a versatile intermediate for the development of multifunctional devices. Interesting chiral discrimination of serine derivatives has been observed, presumably thanks to a multipoint-interaction involving the reversible imine bond formation and the hydrogen bonding of the hydroxyl group of the amino acid side-chain with the upper rim functional groups. Consistently, chiral discrimination was not observed with alanine and valine derivatives, lacking hydrogen bonding groups on the side-chain.
authors.affiliation: Dipartimento di Chimica and IMC - CNR Sezione Meccanismi di Reazione, Università La Sapienza, 00185 Roma, Italy.
authors.forename: Maria
authors.initials: M
authors.lastname: Ciaccia
authors.forename: Irene
authors.initials: I
authors.lastname: Tosi
authors.forename: Roberta
authors.initials: R
authors.lastname: Cacciapaglia
authors.forename: Alessandro
authors.initials: A
authors.lastname: Casnati
authors.forename: Laura
authors.initials: L
authors.lastname: Baldini
authors.forename: Stefano
authors.initials: S
authors.lastname: Di Stefano