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An attractive strategy for generation of α-amino anions from aldehydes with applications in synthesis of homoallylic amines is described. Aromatic aldehydes can be converted to α-amino anion equivalents via amination with 2,2-diphenylglycine and subsequent decarboxylation. The in situ generated α-imino anions are highly reactive for Pd-catalyzed allylation, forming the corresponding homoallylic amines in high yields with excellent regioselectivity.

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This paper describes an efficient method for the synthesis of a-methylidene-g-amino acid esters from readily available aldehydes by using aminative umpolung strategy. Electrophilic aromatic aldehydes were converted to a-imino anions via amination with 2,2-diphenylglycine in methanol and subsequent decarboxylation in acetonitrile. The in situ generated a-imino anions displayed high activity in the reaction with Morita-Baylis-Hillman adducts in the presence of 1,4-diazabicyclo-A C H T U N G T R E N N U N G [2.2.2]octane (DABCO) as catalyst, to give a variety of substituted a-methylidene-g-amino acid esters in 54-96% yields with 3.2-7.1:1 diastereoselectivity. The resulting a-methylidene-g-amino acid esters can be efficiently converted into biologically important a-exo-methylidene-g-lactams under mild conditions.