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Remote Central-to-Axial Chirality Conversion: Direct Atroposelective Ester to Biaryl Transformation
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4495664
Author(s) Link, Achim; Sparr, Christof
Author(s) at UniBasel Sparr, Christof
Link, Achim
Year 2018
Title Remote Central-to-Axial Chirality Conversion: Direct Atroposelective Ester to Biaryl Transformation
Journal Angewandte Chemie International Edition
Volume 57
Number 24
Pages / Article-Number 7136-7139
Abstract A strategy for the remote central-to-axial chirality conversion by simultaneous planarization of an encoding and a transient stereocenter is presented. Based on a diastereoselective double addition of a chiral 1,5-bifunctional organomagnesium alkoxide reagent to a broad range of aryl ester substrates, axially chiral biaryls are directly obtained upon in situ reduction. Various structurally distinct atropisomeric biaryl silanes that serve as valuable chiral biaryl anion surrogates are accessible in one step with e.r.values of up to 98:2.
Publisher Wiley
ISSN/ISBN 1433-7851 ; 1521-3773
edoc-URL https://edoc.unibas.ch/68653/
Full Text on edoc Available
Digital Object Identifier DOI 10.1002/anie.201803472
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/29768705
ISI-Number 000434350400028
Document type (ISI) Journal Article
 
   

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