Published April 7, 2014
| Supplemental Material + Accepted Version
Journal Article
Open
Catalytic, Enantioselective Synthesis of 1,2-anti-Diols by Asymmetric Ring-Opening/Cross-Metathesis
- Creators
- Hartung, John
-
Grubbs, Robert H.
Chicago
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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.
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.Attached Files
Accepted Version - nihms576432.pdf
Supplemental Material - anie_201310767_sm_miscellaneous_information.pdf
Files
anie_201310767_sm_miscellaneous_information.pdf
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Additional details
- Alternative title
- Catalytic, Enantioselective Synthesis of 1,2-anti Diols via Asymmetric Ring Opening/Cross Metathesis
- PMCID
- PMC4037230
- Eprint ID
- 43947
- Resolver ID
- CaltechAUTHORS:20140224-131355335
- NIH
- 5R01GM031332-27
- NSF
- CHE-1048404
- Created
-
2014-03-05Created from EPrint's datestamp field
- Updated
-
2021-11-10Created from EPrint's last_modified field