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

Karim A. Bahou | Zendy; D. Christopher Braddock | Zendy; Adam G. Meyer | Zendy; G. Paul Savage | Zendy

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

Author(s) -

Karim A. Bahou,

D. Christopher Braddock,

Adam G. Meyer,

G. Paul Savage

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b02492

Subject(s) - prenylation , chemistry , olefin metathesis , ruthenium , ring closing metathesis , acceptor , metathesis , olefin fiber , stereochemistry , medicinal chemistry , catalysis , combinatorial chemistry , organic chemistry , enzyme , physics , polymerization , condensed matter physics , polymer

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

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