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Catalyst-Controlled Stereodivergent Synthesis of Atropisomeric Multi-Axis Systems

Lotter, Dominik and Castrogiovanni, Alessandro and Neuburger, Daniel and Sparr, Christof. (2018) Catalyst-Controlled Stereodivergent Synthesis of Atropisomeric Multi-Axis Systems. ACS Central Science, 4 (5). pp. 656-660.

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Official URL: https://edoc.unibas.ch/68652/

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Abstract

Molecular scaffolds with multiple rotationally restricted bonds allow a precise spatial positioning of functional groups. However, their synthesis requires methods addressing the configuration of each stereogenic axis. We report here a catalyst-stereocontrolled synthesis of atropisomeric multiaxis systems enabling divergence from the prevailing stereochemical reaction path. By using ion-pairing catalysts in arene-forming aldol condensations, a strong substrate-induced stereopreference can be overcome to provide structurally well-defined helical oligo-1,2-naphthylenes. The configuration of up to four stereogenic axes was individually catalyst-controlled, affording quinquenaphthalenes with a unique topology.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Sparr)
UniBasel Contributors:Sparr, Christof and Lotter, Dominik and Castrogiovanni, Alessandro and Neuburger, Markus
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:2374-7943
e-ISSN:2374-7951
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:22 Aug 2019 13:09
Deposited On:22 Aug 2019 13:09

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