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Olefin Metathesis in Organic Synthesis
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Short Description: II. Applications of Olefin Metathesis. A. Ring closing metathesis. B. Cross metathesis. C. Ring opening metathesis ... Furstner, A. Topics in Organometallic Chemistry 1998, 1, 1. .... Fundamental Olefin Metathesis React
Content Inside: Olefin Metathesis in Organic Synthesis
Wendy Jen MacMillan Group Meeting January 17, 2001
I. Well-defined alkene metathesis catalysts II. Applications of Olefin Metathesis A. Ring closing metathesis B. Cross metathesis C. Ring opening metathesis
Recent Reviews: Furstner, A. Angew. Chem. Int. Ed. 2000, 39, 3013. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Furstner, A. Topics in Organometallic Chemistry 1998, 1, 1. Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. 1997, 36, 2036
Olefin Metathesis: Introduction
R1 R1 R2 R2
catalyst
R1
R2
R1
R2
! Chauvin-type mechanism: model proceeds through a metallacyclobutane intermediate
R2 [M]
R2
R2 [M]
R2
R2 [M]
R2 R1
R1
R1
! Catalyst systems
WCl6/ EtAlCl2/ EtOH Re2O7/ Al2O3/ SnMe4 WCl6/ Me4Sn Ill-defined catalyst systems Well-defined catalyst systems
Cl Cl PCy3 i-Pr (F3C)2MeCO N
i-Pr
ArO ArO
Ru
PCy3 Ph
Ta
Mo
Ph
ArO
(F3C)2MeCO
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