Witzig, Reto M. and Fäseke, Vincent C. and Häussinger, Daniel and Sparr, Christof. (2019) Atroposelective synthesis of tetra-ortho-substituted biaryls by catalyst-controlled non-canonical polyketide cyclizations. Nature Catalysis , 2 (10). pp. 925-930.
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Official URL: https://edoc.unibas.ch/74207/
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Abstract
The cyclization of poly-β-carbonyl-substrates controlled by polyketide synthases intricately governs the biosynthesis of a wide range of aromatic polyketides. Analogous small-molecule-catalysed processes would conceivably induce selective cyclizations of non-canonical polycarbonyl substrates to provide products distinct from natural polyketides. Here, we report a secondary amine-catalysed twofold cyclization of non-canonical hexacarbonyl substrates, furnishing enantioenriched tetra-ortho-substituted binaphthalenes. The substrates were prepared by a fourfold ozonolysis of dicinnamyl biindenes and converted under catalyst control with high atroposelectivity. Privileged catalysts, helicenes and ligands are readily accessible from the binaphthalene products stemming from the non-canonical polyketide cyclizations.
Faculties and Departments: | 05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Sparr) |
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UniBasel Contributors: | Sparr, Christof and Witzig, Reto and Fäseke, Vincent and Häussinger, Daniel |
Item Type: | Article, refereed |
Article Subtype: | Research Article |
Publisher: | Springer Nature |
e-ISSN: | 2520-1158 |
Note: | Publication type according to Uni Basel Research Database: Journal article |
Language: | English |
Identification Number: |
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edoc DOI: | |
Last Modified: | 01 Jul 2020 12:49 |
Deposited On: | 21 Jan 2020 14:08 |
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