Palladium(0)- and nickel(0) catalyzed "metallo-ene-type" cyclizations: Stereodirecting resident chirality

DOI: 10.1016/S0040-4039(00)88781-X

Source and publish data:

Tetrahedron Letters p. 1265 - 1268 (1990)

Update date:2022-08-04

Topics:

Authors:

Oppolzer, Wolfgang

Keller, Thomas H.

Kuo, David L.

Pachinger, Werner

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Article abstract of DOI:10.1016/S0040-4039(00)88781-X

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.

Full text of DOI:10.1016/S0040-4039(00)88781-X

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