The asymmetric Michael addition of benzoylacetates to cyclic enones was successfully carried out by using a primary β-amino acid salt catalyst. The reactions proceeded under mild reaction conditions to produce Michael adducts in high yields and with high enantioselectivities. The obtained Michael adducts were converted into β-benzoylmethylated cyclic ketones by decarboxylation without a significant loss of enantiomeric excess.
A highly enantioselective Michael addition of β‐ketoesters to enones was achieved by using the salt of a readily available primary β‐amino acid as the catalyst. The obtained Michael adducts were converted into enantioenriched 1,5‐diketones in high yields through a common decarboxylation reaction under acidic conditions. A plausible reaction mechanism for the Michael addition reaction, which is supported by results of mechanistic studies that include DFT calculations, is also described.
Asymmetric Michael Addition of -Ketoesters to Enones Catalyzed by the Lithium Salt of a Primary -Amino Acid. -(YOSHIDA*, M.; KUBARA, A.; NAGASAWA, Y.; HARA, S.; YAMANAKA, M.; Asian J. Org. Chem. 3 (2014) 4, 523-529, http://dx.doi.org/10.1002/ajoc.201400024 ; Div. Chem. Process Eng., Fac. Eng., Hokkaido Univ., Sapporo 060, Japan; Eng.) -Mais 44-023
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