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- Palladium(0)- and nickel(0) catalyzed “metallo-ene-type” cyclizations: Stereodirecting resident chirality.
Oppolzer, W.; Keller, T. H.; Kuo, D. L.; Pachinger, W.
Tetrahedron Lett. 1990, 31, 1265-1268
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 afforded 2-oxa-bicyclo[3.3.0]octanone 12 with highly diastereoselective generation of three stereogenic centers.
DOI : 10.1016/S0040-4039(00)88781-X
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