Abstract
1,3-Disubstituted propanones 4 were prepared by a three-component reaction of 2-methyleneazilizines 1 anchored on the resin with Grignard reagents and electrophiles. Thus, methyleneazilizines 1 reacted with several Grignard reagents in the presence of cupper iodide to form the corresponding metalloenamines 2. The alkylation of metalloenamines 2 with alkyl electrophiles gave ketimine derivatives 3. Filtration and hydrolysis of resin-bound ketimines 3 with pH 4.5 buffer provided the corresponding 1,3-disubstituted propanones 4a-f in 39-81% yields with high purity (91-99%).
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