Stereoselective Alkylation of Cyclic and Acyclic Chiral β-Enamino Ketones Lithium Dianions: Synthesis of Either (R)- or (S)-Chiral 1,3-Diketones.

Article abstract of DOI:10.1016/S0957-4166(00)80373-0

The synthesis of either (R)- or (S)-chiral 1,3-diketones through asymmetric γ alkylation reaction of cyclic and acyclic chiral β-enamino ketones was here performed.The alkylation takes place with good yields and high d.e. in HMPA/THF.Both the pure enantiomers of 1,3-diketones can be formed by simple hydrolysis of the epimeric β-enamino ketones obtained with this method, choosing the suitable synthetic strategies.An explanation of the asymmetric induction was proposed.