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Beilstein J. Org. Chem. 2023, 19, 1443–1451, doi:10.3762/bjoc.19.103
Graphical Abstract
Scheme 1: Air-promoted radical chain reaction of dialkylzinc reagents with α,β-unsaturated carbonyl compounds....
Scheme 2: Enolate formation by zinc radical transfer (SH2 on dialkylzinc reagents).
Scheme 3: Preparation of α-(aminomethyl)acrylate 10.
Scheme 4: Reaction of α-(aminomethyl)acrylate 10 with Et2Zn in the presence of air.
Scheme 5: Chemical correlation to determine the configuration of the major diastereomer of (RS)-14b.
Scheme 6: Air-promoted tandem 1,4-addition–aldol condensation reactions of Et2Zn with α-(aminomethyl)acrylate...
Scheme 7: Diagnostic experiments for a radical mechanism and for enolate formation.
Scheme 8: Diagnostic experiments with N-benzyl enoate 10.
Scheme 9: Reactivity manifolds for the air-promoted tandem 1,4-addition–electrophilic substitution reaction b...