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Published June 8, 2015 | Accepted Version + Supplemental Material
Journal Article Open

Tandem Z-Selective Cross-Metathesis/Dihydroxylation: Synthesis of anti-1,2-Diols


A stereoselective synthesis of anti-1,2-diols has been developed using a multitasking Ru catalyst in an assisted tandem catalysis protocol. A cyclometalated Ru complex catalyzes first a Z-selective cross-metathesis of two terminal olefins, followed by a stereospecific dihydroxylation. Both steps are catalyzed by Ru, as the Ru complex is converted to a dihydroxylation catalyst upon addition of NaIO_4. A variety of olefins were transformed into valuable, highly functionalized, and stereodefined molecules. Mechanistic experiments were performed to probe the nature of the oxidation step and catalyst inhibition pathways. These experiments point the way to more broadly applicable tandem catalytic transformations.

Additional Information

© 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: February 16, 2015; Revised: March 23, 2015. Article first published online: 27 Apr. 2015. This work was financially supported by the ONR (N000141410650), the NIH (5R01M031332-27), and the NSF (CHE-1212767). L. M. Henling is thanked for X-ray crystallography. NMR spectra were obtained using instruments supported by the NIH (RR027690). We thank Dr. J. Hartung for helpful discussions. Materia, Inc. is thanked for the donation of metathesis catalysts.

Attached Files

Accepted Version - nihms711195.pdf

Supplemental Material - anie_201501505_sm_miscellaneous_information.pdf


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