Stereoselective Arene‐Forming Aldol Condensation: Synthesis of Configurationally Stable Oligo‐1,2‐naphthylenes |
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Authors: | Dominik Lotter Dr Markus Neuburger Dr Michel Rickhaus Priv‐Doz?Dr Daniel Häussinger Dr Christof Sparr |
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Institution: | 1. Department of Chemistry, University of Basel, Basel, Switzerland;2. http://www.chemie.unibas.ch/~sparr |
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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. |
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Keywords: | aldol reactions atropisomerism configurational stability oligonaphthylenes stereoselectivity |
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