Organic Letters
Organic Letters
5 years ago

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

Kinetic Benchmarking Reveals the Competence of Prenyl Groups in Ring-Closing Metathesis
G. Paul Savage, Karim A. Bahou, Adam G. Meyer, D. Christopher Braddock
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02492

DOI: 10.1021/acs.orglett.7b02492

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