Published April 14, 2018
| Version Published + Supplemental Material
Journal Article
Open
Using stereoretention for the synthesis of E-macrocycles with ruthenium-based olefin metathesis catalysts
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1.
California Institute of Technology
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.
Additional Information
© 2018 The Royal Society of Chemistry. This Open Access Article is licensed under a Creative Commons Attribution-Non Commercial 3.0 Unported Licence. Received 27th January 2018, Accepted 27th February 2018, First published on 14th March 2018. The authors acknowledge funding from the Office of Naval Research (N00014-14-1-0650), NIH (GM031332), and NSF (CHE-1502616). T. S. A. recognizes NSF for support through a Graduate Research Fellowship. T. P. M. would like to acknowledge the Arnold and Mabel Beckman Foundation for funding. The authors would like to thank W. J. Wolf, C. Xu, C. W. Lee, J. Li, and N. F. Nathel for helpful suggestions. N. Torian and M. Shahgholi are thanked for their help with high-resolution mass spectrometry. Materia, Inc. is acknowledged for generous donations of Ru catalyst precursors. Conflicts of interest: There are no conflicts to declare.Attached Files
Published - c8sc00435h.pdf
Supplemental Material - c8sc00435h1_si.pdf
Files
c8sc00435h.pdf
Additional details
Identifiers
- PMCID
- PMC5934820
- Eprint ID
- 85340
- Resolver ID
- CaltechAUTHORS:20180315-134947702
Funding
- Office of Naval Research (ONR)
- N00014-14-1-0650
- NIH
- GM031332
- NSF
- CHE-1502616
- NSF Graduate Research Fellowship
- Arnold and Mabel Beckman Foundation
Dates
- Created
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2018-03-26Created from EPrint's datestamp field
- Updated
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2022-03-15Created from EPrint's last_modified field