Novel catalytic CO2 incorporation reaction:: Nickel-catalyzed regio- and stereoselective ring-closing carboxylation of bis-1,3-dienes

Novel nickel-catalyzed carboxylation of bis-1,3-dienes using carbon dioxide (CO2) was investigated. In the presence of catalytic amounts of Ni(acac)2 and PPh3, various bis-1,3-dienes smoothly reacted with CO2 and an organozinc reagent (Et2Zn, Me2Zn, or Ph2Zn) under mild conditions. This catalytic carboxylation process was accompanied by carbocyclization of bis-1,3-diene followed by alkylation by an organozinc reagent to afford cyclic carboxylic acid derivatives in high yields with high regio- and stereoselectivities. Copyright © 2002 American Chemical Society.