Kinetic Benchmarking Reveals the Competence of Prenyl Groups in Ring-Closing Metathesis
File(s)7b02492.pdf (302.22 KB)
Accepted version
Author(s)
Bahou, KA
Braddock, DC
Meyer, AG
Savage, GP
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.
Date Issued
2017-09-21
Date Acceptance
2017-09-01
Citation
ORGANIC LETTERS, 2017, 19 (19), pp.5332-5335
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
Identifier
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000412789600083&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Subjects
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