Alkene Metathesis in Organic Synthesis by Alois Fuerstner

By Alois Fuerstner

Content material: Olefin metathesis by means of well-defined complexes of molybdenum and tungsten / R.R.Schrock -- Ruthenium-catalyzed metathesis reactions in natural synthesis / A. Furstner -- Ring-closing metathesis within the synthesis of epothilones and polyether typical items / K.C. Nicolaou, N.P. King, Y. He -- Catalytic ring-closing metathesis and the advance of enantioselective techniques / A.H. Hoveyda -- Enyne metathesis / M. Mori -- Cross-metathesis / Susan E. Gibson, S.P. willing -- contemporary advances in ADMET chemistry / D. Tindall, J.H. Pawlow and K.B. Wagener -- Bioactive polymers / L.L. Kiessling, L.E. robust

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Epothilone A . . . . . . . . . . . . . (+)-Lasiodiplodin . . . . . . . . . . . Tricolorin A . . . . . . . . . . . . . (-)-Gloeosporone: Development of a Binary Metathesis Catalyst System . . . . . . . . . . . . 6 . . . . . . . . . . . . . . . . . . 63 64 64 66 66 . . . . 66 References . . . . . . . . . . . . . . . . . 70 1 Introduction The metathesis activity of various simple ruthenium compounds has already been discerned during early studies on the ring opening metathesis polymerization (ROMP) of norbornene and other cycloalkene substrates [1, 2].

For example, the rate of ethylene evolution in ADMET of [CH2=CH(CH2)3S]2 is lower by a factor of 10 compared to [CH2=CH(CH2)3]2 when Mo is employed, but is essentially zero when Ru is employed. It is surprising that the rate of metathesis by Ru is so dramatically attenuated in the presence of donors such as O, S, CN, or amines, while the rate of metathesis by MoF6 is much less so. A casual analysis would have suggested that the opposite would be true. Both Mo and Ru catalysts have begun to show their utility in organic synthesis involving RCM.

Propagation is approximately an order of magnitude faster than initiation for steric reasons, while the relatively slow rate of chain transfer relative to propagation can be accounted for on the basis of the high reactivity of norbornene. Since both syn and anti rotamers are accessible in the t-butoxide system, it is uncertain to which rotamers these rate constants refer. The mixture of cis and trans double bonds in the resulting poly(norbornene) could be taken as evidence that both rotamers of the living polymer are involved.

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