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

Autor: Bahou KA; Department of Chemistry, Imperial College London , South Kensington, London SW7 2AZ, U.K., Braddock DC; Department of Chemistry, Imperial College London , South Kensington, London SW7 2AZ, U.K., Meyer AG; CSIRO Manufacturing, Private Bag 10, Clayton South VIC 3169, Australia., Savage GP; CSIRO Manufacturing, Private Bag 10, Clayton South VIC 3169, Australia.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2017 Oct 06; Vol. 19 (19), pp. 5332-5335. Date of Electronic Publication: 2017 Sep 21.
DOI: 10.1021/acs.orglett.7b02492
Abstrakt: 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.
Databáze: MEDLINE