Hydrogen Bond Templated 1:1 Macrocyclization through an Olefin Metathesis/Hydrogenation Sequence

The construction of pyridine-containing macrocyclic architectures using a nonmetallic template is described. 4,6-Dichlororesorcinol was used as an exotemplate to self-organize two aza-heterocyclic units by OH···N hydrogen bonds. Subsequent sequential double olefin metathesis/hydrogenation reactions...

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Bibliographic Details
Published in:Organic letters 2013-07, Vol.15 (14), p.3798-3801
Main Authors: Trita, Andrada Stefania, Roisnel, Thierry, Mongin, Florence, Chevallier, Floris
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Catalysis
Chemical Sciences
Cyclization
Hydrogen Bonding
Hydrogenation
Macrocyclic Compounds - chemistry
Molecular Structure
Other
Pyridines - chemistry
Resorcinols - chemistry
Ruthenium - chemistry
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Summary:The construction of pyridine-containing macrocyclic architectures using a nonmetallic template is described. 4,6-Dichlororesorcinol was used as an exotemplate to self-organize two aza-heterocyclic units by OH···N hydrogen bonds. Subsequent sequential double olefin metathesis/hydrogenation reactions employing a single ruthenium–alkylidene precatalyst open access to macrocyclic molecules.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401803t