Novel Catalytic CO(2) Incorporation Reaction: Nickel-Catalyzed Regio- and Stereoselective Ring-Closing Carboxylation of Bis-1,3-dienes

Masanori Takimoto; Miwako Mori

doi:10.1021/ja026620c

Novel Catalytic CO(2) Incorporation Reaction: Nickel-Catalyzed Regio- and Stereoselective Ring-Closing Carboxylation of Bis-1,3-dienes

J Am Chem Soc. 2002 Aug 28;124(34):10008-9. doi: 10.1021/ja026620c.

Authors

Masanori Takimoto¹, Miwako Mori

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.

PMID: 12188663
DOI: 10.1021/ja026620c

Abstract

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.