Alois Fuerstner's Alkene Metathesis in Organic Synthesis PDF

By Alois Fuerstner

ISBN-10: 3540642544

ISBN-13: 9783540642541

Content material: Olefin metathesis by way 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 average items / K.C. Nicolaou, N.P. King, Y. He -- Catalytic ring-closing metathesis and the advance of enantioselective procedures / 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. powerful

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Extra resources for Alkene Metathesis in Organic Synthesis

Example text

The metallacycle formation is the rate determining step. The observed reactivity pattern of the pre-catalyst outlined above and the kinetic data presently available support this mechanistic picture. The fact that the catalytic activity of ruthenium carbene complexes 1 may be significantly enhanced on addition of CuCl to the reaction mixture is also very well in line with this dissociative mechanism [11]: Cu(I) is known to trap phosphines and its presence may therefore lead to a higher concentration of the catalytically active monophosphine metal fragments F and G in solution.

Even unprotected alcohols and free carboxylic acids seem to be tolerated by 1. It should also be emphasized that the sensitivity of 1 toward the substitution pattern of alkenes outlined above usually leaves pre-existing di-, tri- and tetrasubstituted double bonds in the substrates unaffected. A nice example that illustrates many of these features is the clean dimerization of FK-506 45 to compound 46 reported by Schreiber et al. (Scheme 12) [27]. Problematic functional groups, however, are thioethers and disulfides [28] as well as free amines which poison catalysts of type 1 [4c].

Buffon R, Leconte M, Choplin A, Basset J-M (1993) J Chem Soc, Chem Commun 361 114. Weiss K, Lössel G (1989) Angew Chem, Int Ed Engl 28:62 115. Herrmann WA, Stumpf AW, Priermeier T, Bogdanovic S, Dufaud V, Basset JM (1997) Angew Chem Int Ed 35:2803 116. Crowe WE, Zhang ZJ (1993) J Am Chem Soc 115:10998 117. Crowe WE, Goldberg DR (1995) J Am Chem Soc 117:5162 118. Crowe WE, Goldberg DR, Zhang ZJ (1996) Tetrahedron Lett 37:2117 119. Brümmer O, Rückert A, Blechert S (1997) Chem-Eur J 3:441 120. Barrett AGM, Beall JC, Gibson VC, Giles MR, Walker GLP (1996) Chem Commun 2229 121.

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Alkene Metathesis in Organic Synthesis by Alois Fuerstner

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