Alkene Metathesis in Organic Synthesis by Alois Fuerstner

By Alois Fuerstner

Content material: Olefin metathesis via 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 average items / K.C. Nicolaou, N.P. King, Y. He -- Catalytic ring-closing metathesis and the improvement of enantioselective approaches / A.H. Hoveyda -- Enyne metathesis / M. Mori -- Cross-metathesis / Susan E. Gibson, S.P. willing -- fresh advances in ADMET chemistry / D. Tindall, J.H. Pawlow and K.B. Wagener -- Bioactive polymers / L.L. Kiessling, L.E. powerful

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39 43 46 3 The Application Profile of the Standard Ruthenium-Based Metathesis Catalysts in Synthesis . . . . . . . . . . 5 Effects of Olefin Substitution . . . . . Functional Group Compatibility . . . . Ring Size . . . . . . . . . . . Sequential Transformations . . . . . . Metathesis Reactions in Solid Phase Synthesis . . . 46 51 51 58 59 4 Olefin Metathesis in Supercritical Carbon Dioxide . . . . . 59 . . . . . . . . . . . . . .

2 Scheme 4. (ROMP) of functionalized oxanorbornenes in water, methanol and aqueous emulsions, but have not yet been used in RCM. The overall mechanism of RCM is generally believed to proceed via the alternating series of formal [2+2] cycloaddition/cycloreversion steps outlined in Scheme 4 (Chauvin mechanism) [1, 13], although many details concerning the structure and properties of the intermediates A–D involved in this catalytic cycle are not yet fully resolved. Only recently, an in-depth study provided some insights into the actual nature of such intermediates [11].

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].

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