132. Metal-directed stereoselective functionalization of alkenes in organic synthesis
     Oppolzer, W.
     Pure Appl. Chem. 1988, 60, 39-48

The critical role of metals in π-face selective alkene functionalizations is exemplified by Diels-Alder reactions, osmylations, hydrogenations, conjugate additions (hydride, organocopper reagents, alkylmagnesium halides) of N-enoyl-bornane-10,2-sultams as well as by protonations, alkylations and aldolizations of “enolates” derived from the same auxiliary. In extension of the magnesium-ene process catalytic intramolecular palladium-ene reactions are presented. Thus, Pd(dba)₂/PPh₃- or Pd(PPh)₃-catalyzed stereoselective cyclizations of acetoxy-2,7(8)-dienes gave 1-vinyl-2-methylene- or 1,2-divinyl-substituted cyclopentanes (or cyclohexanes) consistent with a cis-insertion/β-elimination process.

DOI : 10.1351/pac198860010039 

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