Xu, Yan and Gan, Quan and Samkian, Adrian E. and Ko, Jeong Hoon and Grubbs, Robert H. (2022) Bulky Cyclometalated Ruthenium Nitrates for Challenging Z‐Selective Metathesis: Efficient One‐Step Access to α‐Oxygenated Z‐Olefins from Acrylates and Allyl Alcohols. Angewandte Chemie International Edition, 61 (4). Art. No. e202113089. ISSN 1433-7851. doi:10.1002/anie.202113089. https://resolver.caltech.edu/CaltechAUTHORS:20211207-6358000
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Abstract
α-Oxygenated Z-olefins are ubiquitous in biologically active molecules and serve as versatile handles for organic synthesis, but their syntheses are often tedious and less selective. Here we report the efficient Z-selective metathesis of various terminal acrylates and allyl alcohols, which enables facile and selective construction of high value-added α-oxygenated Z-olefins from readily available feedstock chemicals. These challenging metathesis transformations are enabled by novel cyclometalated Ru-carbene-nitrate complexes bearing bulky-yet-flexible side arms, whose assembly was unlocked by new organometallic syntheses.
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| Additional Information: | © 2021 Wiley-VCH. Issue Online: 14 January 2022; Version of Record online: 07 December 2021; Accepted manuscript online: 14 November 2021; Manuscript received: 27 September 2021. We gratefully acknowledge Umicore for financial support. This research was benefited from the use of instrumentation made available by the Caltech CCE Multiuser Mass Spectrometry Laboratory, and Dr. Mona Shahgoli is thanked for assistance with HRMS experiments. Dr. Adam Johns and Dr. Jianchun Wang are acknowledged for helpful discussions. The authors declare no conflict of interest. | ||||||||||||
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| Subject Keywords: | Acrylates; Allyl alcohols; α-Oxygenated Z-olefins; Ruthenium; Z-selective olefin-metathesis | ||||||||||||
| Issue or Number: | 4 | ||||||||||||
| DOI: | 10.1002/anie.202113089 | ||||||||||||
| Record Number: | CaltechAUTHORS:20211207-6358000 | ||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20211207-6358000 | ||||||||||||
| Official Citation: | Bulky Cyclometalated Ruthenium Nitrates for Challenging Z‐Selective Metathesis: Efficient One‐Step Access to α‐Oxygenated Z‐Olefins from Acrylates and Allyl Alcohols Y. Xu, Q. Gan, A. E. Samkian, J. H. Ko, R. H. Grubbs, Angew. Chem. Int. Ed. 2022, 61, e202113089; DOI: 10.1002/anie.202113089 | ||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||
| ID Code: | 112271 | ||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||
| Deposited By: | George Porter | ||||||||||||
| Deposited On: | 10 Dec 2021 22:37 | ||||||||||||
| Last Modified: | 18 Jan 2022 23:23 |
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