Hartung, John and Grubbs, Robert H. (2014) Catalytic, Enantioselective Synthesis of 1,2-anti-Diols by Asymmetric Ring-Opening/Cross-Metathesis. Angewandte Chemie International Edition, 53 (15). pp. 3885-3888. ISSN 1433-7851. PMCID PMC4037230. doi:10.1002/anie.201310767. https://resolver.caltech.edu/CaltechAUTHORS:20140224-131355335
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Abstract
An enantioselective method for the synthesis of 1,2-anti-diols has been developed. A cyclometalated chiral-at-ruthenium complex catalyzes the asymmetric ring-opening/cross-metathesis of dioxygenated cyclobutenes, thus resulting in functionally rich synthetic building blocks. Syntheses of the insect pheromone (+)-endo-brevicomin and monosaccharide ribose demonstrate the synthetic utility of the 1,2-anti-diol fragments generated in the title reaction.
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| Alternate Title: | Catalytic, Enantioselective Synthesis of 1,2-anti Diols via Asymmetric Ring Opening/Cross Metathesis | ||||||||||||
| Additional Information: | © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: December 11, 2013; Article first published online: 19 Feb. 2014. This work was financially supported by the NIH (5R01GM031332-27 to R.H.G.) and the NSF (CHE-1048404 to R.H.G.). We thank Materia, Inc. for donation of metathesis catalysts and Dr. Jeffrey Cannon, Dr. Bill Morandi, and Zach K. Wickens for helpful discussion. | ||||||||||||
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| Subject Keywords: | alcohols; asymmetric catalysis; metathesis; pheromones; ruthenium | ||||||||||||
| Issue or Number: | 15 | ||||||||||||
| PubMed Central ID: | PMC4037230 | ||||||||||||
| DOI: | 10.1002/anie.201310767 | ||||||||||||
| Record Number: | CaltechAUTHORS:20140224-131355335 | ||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20140224-131355335 | ||||||||||||
| Official Citation: | Hartung, J. and Grubbs, R. H. (2014), Catalytic, Enantioselective Synthesis of 1,2-anti-Diols by Asymmetric Ring-Opening/Cross-Metathesis. Angew. Chem. Int. Ed., 53: 3885–3888. doi: 10.1002/anie.201310767 | ||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||
| ID Code: | 43947 | ||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||
| Deposited By: | Tony Diaz | ||||||||||||
| Deposited On: | 05 Mar 2014 18:55 | ||||||||||||
| Last Modified: | 10 Nov 2021 16:45 |
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