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Synthesis of Atropisomeric Two-Axis Systems by the Catalyst-Controlled syn- and anti-Selective Arene-Forming Aldol Condensation
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4650935
Author(s) Moser, Daniel; Sparr, Christof
Author(s) at UniBasel Sparr, Christof
Year 2022
Title Synthesis of Atropisomeric Two-Axis Systems by the Catalyst-Controlled syn- and anti-Selective Arene-Forming Aldol Condensation
Journal Angewandte Chemie International Edition
Volume 61
Number 24
Pages / Article-Number e202202548
Keywords Aldolizations; Atropisomers; Cyclizations; Polyketides; Stereoselectivity
Mesh terms Aldehydes; Catalysis; Cinchona Alkaloids; Stereoisomerism
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.
Publisher Wiley
ISSN/ISBN 1433-7851 ; 1521-3773
edoc-URL https://edoc.unibas.ch/90233/
Full Text on edoc Available
Digital Object Identifier DOI 10.1002/anie.202202548
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/35343034
ISI-Number 000783274000001
Document type (ISI) Journal Article
 
   

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12/05/2024