title: Stereoselective Arene-Forming Aldol Condensation: Synthesis of Configurationally Stable Oligo-1,2-naphthylenes.
abstract: Structurally well-defined oligomers are fundamental for the functionality of natural molecular systems and key for the design of synthetic counterparts. Herein, we describe a strategy for the efficient synthesis of individual stereoisomers of 1,2-naphthylene oligomers by iterative building block additions and consecutive stereoselective arene-forming aldol condensation reactions. The catalyst-controlled atropoenantioselective and the substrate-controlled atropodiastereoselective aldol condensation reaction provide structurally distinct ter- and quaternaphthalene stereoisomers, which represent configurationally stable analogues of otherwise stereodynamic, helically shaped ortho-phenylenes.
authors.affiliation: Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland.
authors.forename: Dominik
authors.initials: D
authors.lastname: Lotter
authors.affiliation: Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland.
authors.forename: Markus
authors.initials: M
authors.lastname: Neuburger
authors.affiliation: Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland.
authors.forename: Michel
authors.initials: M
authors.lastname: Rickhaus
authors.affiliation: Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland.
authors.forename: Daniel
authors.initials: D
authors.lastname: Häussinger
authors.affiliation: Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland. christof.sparr@unibas.ch.
authors.forename: Christof
authors.initials: C
authors.lastname: Sparr
keywords: aldol reactions; atropisomerism; configurational stability; oligonaphthylenes; stereoselectivity