Moser, Daniel and Sparr, Christof. (2022) Synthesis of Atropisomeric Two-Axis Systems by the Catalyst-Controlled syn- and anti-Selective Arene-Forming Aldol Condensation. Angewandte Chemie International Edition, 61 (24). e202202548.
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Abstract
Simultaneous control over the configuration of multiple stereocenters is accomplished by numerous catalytic methods, providing a reliable basis for the synthesis of stereochemically complex targets in isomerically defined form. In contrast, addressing the configurations of multiple stereogenic axes with diastereodivergent catalyst control is thus far only possible by stepwise approaches. Herein we now describe that all four stereoisomers of atropisomeric two-axis systems are directly tractable by assembling a central aromatic unit of teraryls through an arene-forming aldol condensation. By using cinchona alkaloid-based ion-pairing catalysts, the four feasible reaction pathways are differentiated from identical substrates under defined basic conditions without preactivation, thus enabling complete stereodivergence with enantioselectivities of up to 99 : 1 e.r.
Faculties and Departments: | 05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Sparr) |
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UniBasel Contributors: | Sparr, Christof |
Item Type: | Article, refereed |
Article Subtype: | Research Article |
Publisher: | Wiley |
ISSN: | 1433-7851 |
e-ISSN: | 1521-3773 |
Note: | Publication type according to Uni Basel Research Database: Journal article |
Language: | English |
Identification Number: |
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edoc DOI: | |
Last Modified: | 16 Nov 2022 08:16 |
Deposited On: | 16 Nov 2022 08:16 |
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