Synthesis of beta-lactones: a highly active and selective catalyst for epoxide carbonylation |
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Authors: | Getzler Yutan D Y L Mahadevan Viswanath Lobkovsky Emil B Coates Geoffrey W |
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Institution: | Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853, USA. |
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Abstract: | A new highly active and selective catalyst for the synthesis of beta-lactones from CO and epoxides is reported. The catalyst, (N,N'-bis(3,5-di-tert-butylsalicylidene) phenylenediamino)Al(THF)2]Co(CO)4] ((salph)Al(THF)2]Co(CO)4]) is easily prepared from the corresponding (salph)AlCl and NaCo(CO)4. At 50 degrees C and 880 psi of CO, the catalyst (1 mol %) carbonylates epoxides such as propylene oxide, 1-butene oxide, epichlorohydrin, and isobutylene oxide to the lactones beta-butyrolactone, beta-valerolactone, gamma-chloro-beta-butyrolactone, and beta-methyl-beta-butyrolactone in high yield. (R)-Propylene oxide was carbonylated to (R)-beta-butyrolactone with retention of stereochemistry. |
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