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Metal-directed stereoselective functionalization of alkenes in organic synthesis

Published inPure and applied chemistry, vol. 60, no. 1, p. 39-48
Publication date1988-01-01
First online date2009-01-01
Abstract

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.

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Citation (ISO format)
VON OPPOLZER, Wolfgang. Metal-directed stereoselective functionalization of alkenes in organic synthesis. In: Pure and applied chemistry, 1988, vol. 60, n° 1, p. 39–48. doi: 10.1351/pac198860010039
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ISSN of the journal0033-4545
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