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

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.

SUBMITTER: Ahmed TS

PROVIDER: S-EPMC5934820 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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

Ahmed Tonia S TS Montgomery T Patrick TP Grubbs Robert H RH

Chemical science 20180314 14

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 die ...[more]

PMID: 29780490

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