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Tandem metathesis- dihydroxylation and metathesis- oxidative cyclization reactions

Dornan, Peter and Wickens, Zachary and Lee, Daniel and Blumenfeld, Carl and Grubbs, Robert (2016) Tandem metathesis- dihydroxylation and metathesis- oxidative cyclization reactions. In: 251st American Chemical Society National Meeting & Exposition, March 13-17, 2016, San Diego, CA. https://resolver.caltech.edu/CaltechAUTHORS:20160331-090714454

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Abstract

Tandem catalysis provides an opportunity to assemble significant mol. complexity via mechanistically distinct reactions with a single catalyst. We have developed a tandem Z- selective cross metathesis - dihydroxylation, and have explored the substrate specificity of the catalytic system. We have also developed a tandem metathesis - oxidative cyclization to assemble THF diol motifs. Due to the stereospecificity of the oxidn. step, the product stereochem. is detd. in part by the olefin geometry. The stereochem. of the olefin in turn is detd. by the type of metathesis performed and choice of catalyst. The reaction scope and applications of the oxidative cyclization will be explored. Mechanistic comparisons between dihydroxylation and oxidative cyclization will also be discussed, specifically with regards to the nature of the ruthenate ester hydrolysis step.


Item Type:Conference or Workshop Item (Paper)
Related URLs:
URLURL TypeDescription
http://www.acs.org/content/acs/en/meetings/spring-2016.htmlOrganizationConference Website
ORCID:
AuthorORCID
Lee, Daniel0000-0001-7411-2740
Grubbs, Robert0000-0002-0057-7817
Additional Information:© 2016 American Chemical Society.
Record Number:CaltechAUTHORS:20160331-090714454
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160331-090714454
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:65793
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:31 Mar 2016 17:45
Last Modified:03 Oct 2019 09:50

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