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
The nitrogen substituent, thus leading to the selective formation of 34 or 35, respectively (Scheme 10) . 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  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 .