Catalytic carbonylation of beta-lactones to succinic anhydrides

Yutan D Y L Getzler; Vinod Kundnani; Emil B Lobkovsky; Geoffrey W Coates

doi:10.1021/ja048946m

Catalytic carbonylation of beta-lactones to succinic anhydrides

J Am Chem Soc. 2004 Jun 9;126(22):6842-3. doi: 10.1021/ja048946m.

Authors

Yutan D Y L Getzler¹, Vinod Kundnani, Emil B Lobkovsky, Geoffrey W Coates

Affiliation

¹ Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.

PMID: 15174834
DOI: 10.1021/ja048946m

Abstract

A well-defined, highly active and selective catalyst for the synthesis of succinic anhydrides from CO and beta-lactones is reported. At 200 psi of CO, the catalyst [(N,N'-bis(3,5-di-tert-butylsalicylidene)phenylenediamino)Al(THF)2][Co(CO)4] carbonylates beta-propiolactones to succinic anhydrides in high yield. (R)-beta-Butyrolactone is carbonylated to (S)-methylsuccinic anhydride with clean inversion of stereochemistry, while cis-2,3-dimethyl-beta-propiolactone yields exclusively trans-2,3-dimethylsuccinic anhydride. These data are consistent with a mechanism involving nucleophilic attack by [Co(CO)4]- on the beta carbon of the lactone, followed by CO insertion and anhydride formation.