Scientific article
Open access

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

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.

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
Main files (1)
Article (Published version)
ISSN of the journal0033-4545

Technical informations

Creation10/19/2021 8:32:00 AM
First validation10/19/2021 8:32:00 AM
Update time03/16/2023 1:35:43 AM
Status update03/16/2023 1:35:42 AM
Last indexation01/29/2024 10:50:37 PM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack