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Catalytic, Enantioselective Synthesis of 1,2-anti-Diols by Asymmetric Ring-Opening/Cross-Metathesis

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.

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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.

Item Type:Article
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URLURL TypeDescription CentralArticle
Grubbs, Robert H.0000-0002-0057-7817
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.
Funding AgencyGrant Number
Subject Keywords:alcohols; asymmetric catalysis; metathesis; pheromones; ruthenium
Issue or Number:15
PubMed Central ID:PMC4037230
Record Number:CaltechAUTHORS:20140224-131355335
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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
Deposited By: Tony Diaz
Deposited On:05 Mar 2014 18:55
Last Modified:10 Nov 2021 16:45

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