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Bulky Cyclometalated Ruthenium Nitrates for Challenging Z‐Selective Metathesis: Efficient One‐Step Access to α‐Oxygenated Z‐Olefins from Acrylates and Allyl Alcohols

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/anie.202113089DOIArticle
ORCID:
AuthorORCID
Xu, Yan0000-0003-2808-7964
Gan, Quan0000-0001-5908-4163
Samkian, Adrian E.0000-0002-0068-3572
Ko, Jeong Hoon0000-0003-2000-3789
Grubbs, Robert H.0000-0002-0057-7817
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.
Funders:
Funding AgencyGrant Number
UmicoreUNSPECIFIED
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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