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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 traditional items / K.C. Nicolaou, N.P. King, Y. He -- Catalytic ring-closing metathesis and the improvement of enantioselective tactics / A.H. Hoveyda -- Enyne metathesis / M. Mori -- Cross-metathesis / Susan E. Gibson, S.P. prepared -- 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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Extra info for Alkene Metathesis in Organic Synthesis

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The nitrogen substituent, thus leading to the selective formation of 34 or 35, respectively (Scheme 10) [21]. Polar substituents on the double bonds of a given substrate – both electron donating and electron withdrawing ones – usually stop the catalytic process [5d]. Among the (few) exceptions to this rule are cyclization reactions involving α,β-unsaturated esters or amides (Scheme 11) as exemplified by the formal total synthesis of the glucosidase inhibitor castanospermine 38 [22] and by the formation of compound 40 starting from triene 39.

When A (OR=acetate) was taken to 90% conversion, the ee of residual A was 84%. The relatively low enantioselectivity might be ascribed to the slow interconversion of syn and anti rotamers of the intermediates or to the relatively “floppy” nature of the diolate that forms a pseudo nine-membered ring containing the metal. OR Mo* OR OR + A OR Mo* OR OR + B (45) - (46) 30 Richard R. Schrock A Mo catalyst that contains an enantiomerically pure binaphtholate or biphenolate ligand would seem to have a better opportunity for ARCM since the ligand forms a relatively rigid pseudo six-membered ring containing the metal and syn and anti rotamers are known to interconvert readily.

38 2 Synthesis, Structure, Mechanism and Activity of Ruthenium-Based Metathesis Catalysts . . . . . . . . 3 Ruthenium Carbene Complexes and General Aspects of RCM . . Ruthenium Allenylidene Complexes . . . . . . . . . Less Defined Ruthenium Catalysts . . . . . . . . . . 39 43 46 3 The Application Profile of the Standard Ruthenium-Based Metathesis Catalysts in Synthesis . . . . . . . . . . 5 Effects of Olefin Substitution . . . . . Functional Group Compatibility .

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