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Ring-Closing Metathesis on Solid Support: Elaboration of a Cyclization/Cleavage Strategy Towards Unsaturated α-Ester-Substituted N-Heterocycles

1998; Wiley; Volume: 1998; Issue: 11 Linguagem: Inglês

10.1002/(sici)1099-0690(199811)1998

1434-193X

Johan J. N. Veerman, Jan H. van Maarseveen, Geb M. Visser, Chris G. Kruse, Hans E. Schoemaker, Henk Hiemstra, Floris P. J. T. Rutjes,

Synthesis and Catalytic Reactions

A Ru-mediated strategy for the cleavage of organic substrate molecules from a solid support via ring-closing metathesis is described. Application of this protocol to solid phase-bound olefinic amino acid derivatives provides various highly functionalized unsaturated N-heterocycles of different ring-sizes in moderate to excellent yields. This strategy features the addition of a stoichiometric amount of styrene to the metathesis mixture, which is shown to increase the yield of the reaction.