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Issue 14, 2018
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Using stereoretention for the synthesis of E-macrocycles with ruthenium-based olefin metathesis catalysts

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Abstract

The synthesis of E-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 4 providing meaningful yields of products in much shorter reaction times than stereoretentive catalysts 2 and 3. Macrocycles were generated with excellent selectivity (>99% E) and in moderate to high yields (47–80% yield) from diene starting materials bearing two E-configured olefins. A variety of rings were constructed, ranging from 12- to 18-membered macrocycles, including the antibiotic recifeiolide.

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

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Supplementary files

Article information


Submitted
27 Jan 2018
Accepted
27 Feb 2018
First published
14 Mar 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 3580-3583
Article type
Edge Article

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

T. S. Ahmed, T. P. Montgomery and R. H. Grubbs, Chem. Sci., 2018, 9, 3580
DOI: 10.1039/C8SC00435H

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