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Optically pure disubstituted dialkenic amides 2, which are direct precursors of Z-ethylenic pseudopeptides 1, are readily synthesized and then cyclized to lactams 3 in the presence of Grubbs' ruthenium-based metathesis catalysts with total conservation of enantiomeric purity.
We show here the first example of a ruthenium catalyzed ene-yne metathesis reaction in tandem with a Diels-Alder cycloaddition reaction to efficiently form highly substituted hexahydroisoindole ring systems on Wang resin. This approach was used to prepare a 4200 membered combinatorial library.
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