Tetrahedron Letters p. 1265 - 1268 (1990)
Update date:2022-08-04
Topics:
Oppolzer, Wolfgang
Keller, Thomas H.
Kuo, David L.
Pachinger, Werner
Trans-cyclization products were selectively formed from C-6-substituted acetoxy-octadienes only via Ni(0) catalysis (1 → 2) and from C-4-substituted analogs under Pd(0)- and Ni(0) catalysis (7, 8 → 9). C-5-Substituted precursors gave mixtures of diastereoisomers. Nickel(0) catalyzed allylation/methoxycarbonylation of iodo diene 11 afforded 2-oxa-bicyclo[3.3.0]octanone 12 with highly diastereoselective generation of three stereogenic centers.
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