Highly enantioselective catalytic carbon dioxide incorporation reaction: nickel-catalyzed asymmetric carboxylative cyclization of bis-1,3-dienes

Masanori Takimoto; Yoichi Nakamura; Kaoru Kimura; Miwako Mori

doi:10.1021/ja049506y

Highly enantioselective catalytic carbon dioxide incorporation reaction: nickel-catalyzed asymmetric carboxylative cyclization of bis-1,3-dienes

J Am Chem Soc. 2004 May 19;126(19):5956-7. doi: 10.1021/ja049506y.

Authors

Masanori Takimoto¹, Yoichi Nakamura, Kaoru Kimura, Miwako Mori

Affiliation

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

PMID: 15137747
DOI: 10.1021/ja049506y

Abstract

A method for nickel-catalyzed asymmetric carbon dioxide (CO2) incorporation via carbon-carbon bond formation was developed. In the presence of a catalytic amount of Ni(acac)2 and MeO-MOP, various bis-1,3-dienes reacted with CO2 (1 atm) and a diorganozinc reagent (Me2Zn or Ph2Zn) to afford cyclic carboxylic acids in good yields (71-100%) and with high enantioselectivities (90-96% ee).