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Kinetic Benchmarking Reveals the Competence of Prenyl Groups in Ring-Closing Metathesis

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Title: Kinetic Benchmarking Reveals the Competence of Prenyl Groups in Ring-Closing Metathesis
Authors: Bahou, KA
Braddock, DC
Meyer, AG
Savage, GP
Item Type: Journal Article
Abstract: A series of prenyl-containing malonates are kinetically benchmarked against the standard allyl-containing congeners using a ruthenium benzylidene precatalyst for ring-closing metatheses. The prenyl grouping is found to be a superior acceptor olefin compared to an allyl group in RCM processes with ruthenium alkylidenes derived from terminal alkenes. The prenyl group is also found to be a highly competent acceptor for a ruthenium alkylidene derived from a 1,1-disubstituted olefin in a RCM process.
Issue Date: 21-Sep-2017
Date of Acceptance: 1-Sep-2017
URI: http://hdl.handle.net/10044/1/53442
DOI: https://dx.doi.org/10.1021/acs.orglett.7b02492
ISSN: 1523-7060
Publisher: American Chemical Society
Start Page: 5332
End Page: 5335
Journal / Book Title: ORGANIC LETTERS
Volume: 19
Issue: 19
Copyright Statement: © 2017 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/acs.orglett.7b02492
Keywords: Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
RUTHENIUM-INDENYLIDENE COMPLEXES
ENANTIOSELECTIVE TOTAL-SYNTHESIS
1ST ENANTIOSPECIFIC SYNTHESIS
OLEFIN METATHESIS
ALLYLIC ALCOHOLS
ASYMMETRIC-SYNTHESIS
CROSS-METATHESIS
NHC LIGAND
STRATEGY
CATALYSTS
03 Chemical Sciences
Organic Chemistry
Publication Status: Published
Appears in Collections:Chemistry
Faculty of Natural Sciences