Using stereoretention for the synthesis of E -macrocycles with ruthenium-based olefin metathesis catalysts

The synthesis of -macrocycles is achieved using stereoretentive, Ru-based olefin metathesis catalysts supported by dithiolate ligands. Kinetic studies elucidate marked differences in activity among the catalysts tested, with catalyst providing meaningful yields of products in much shorter reaction t...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2018-04, Vol.9 (14), p.3580-3583
Main Authors: Ahmed, Tonia S, Montgomery, T Patrick, Grubbs, Robert H
Format: Article
Language:English
Subjects:
Alkenes
Antibiotics
Catalysis
Catalysts
Chemical synthesis
Decomposition reactions
Metathesis
Ruthenium
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Summary:The synthesis of -macrocycles is achieved using stereoretentive, Ru-based olefin metathesis catalysts supported by dithiolate ligands. Kinetic studies elucidate marked differences in activity among the catalysts tested, with catalyst providing meaningful yields of products in much shorter reaction times than stereoretentive catalysts and . Macrocycles were generated with excellent selectivity (>99% ) and in moderate to high yields (47-80% yield) from diene starting materials bearing two -configured olefins. A variety of rings were constructed, ranging from 12- to 18-membered macrocycles, including the antibiotic recifeiolide.
ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc00435h