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Atroposelective Arene-Forming Alkene Metathesis
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4650932
Author(s) Jončev, Zlatko; Sparr, Christof
Author(s) at UniBasel Sparr, Christof
Year 2022
Title Atroposelective Arene-Forming Alkene Metathesis
Journal Angewandte Chemie International Edition
Volume 61
Number 51
Pages / Article-Number e202211168
Keywords Atropisomerism; Catalysis; metathesis; stereoselectivity; traceless
Mesh terms Alkenes, chemistry; Stereoisomerism; Catalysis; Molybdenum, chemistry; Coordination Complexes
Abstract Alkene metathesis catalyzed by enantiopure metal alkylidene complexes enables exceptionally versatile strategies to products with configurationally-defined stereocenters. Desymmetriza-tion processes thereby provide reliable stereoselective routes to aliphatic structures, while the differentiation of aromatic stereogenic units remained an outstanding challenge. Herein, we describe the feasibility of alkene metathesis to catalytically control stereogenic axes by traceless arene formation. Stereodynamic trienes are selectively converted into corresponding binaphthalene atropisomers upon exposure to a chiral molybdenum catalyst. Remarkably, stereo-selective arene-forming metathesis allows enantioselectivities of up to 98:2 e.r. and excellent yields. As the disconnection of each bond of an aromatic target is retrosynthetically conceivable, it is anticipated that forging arenes by means of stereoselective metathesis will enable versatile approaches for the synthesis of a broad range of molecular topologies with precisely defined configuration.
Publisher Wiley
ISSN/ISBN 1433-7851 ; 1521-3773
edoc-URL https://edoc.unibas.ch/90230/
Full Text on edoc Available
Digital Object Identifier DOI 10.1002/anie.202211168
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/36283028
ISI-Number 000888913500001
Document type (ISI) Journal Article
 
   

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12/05/2024