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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


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


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