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Catalytic Z ‐Selective Cross‐Metathesis with Secondary Silyl‐ and Benzyl‐Protected Allylic Ethers: Mechanistic Aspects and Applications to Natural Product Synthesis
Author(s) -
Mann Tyler J.,
Speed Alexander W. H.,
Schrock Richard R.,
Hoveyda Amir H.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201302538
Subject(s) - allylic rearrangement , silylation , catalysis , natural product , alkyne , metathesis , olefin fiber , combinatorial chemistry , chemistry , organic chemistry , polymerization , polymer
Get me a Z (olefin) : Efficient catalytic cross‐metathesis reactions that afford Z ‐disubstituted allylic silyl or benzyl ethers are reported (see scheme, MAP=monoalkoxide pyrrolide). The approach, in combination with catalytic cross‐coupling, provides a general entry to otherwise difficult‐to‐access alkyne‐containing Z olefins.