Abstract
A study on the asymmetric construction of quaternary stereogenic centers via [2 + 2] cycloaddition reaction of ketenes with ketimines is described. Reaction of achiral ketenes and chiral alpha-alkoxy ketone-derived imines resulted in formation of new beta-lactams as single diastereomers. The cycloaddition was extended to pyruvate imines, aralkyl ketone-derived imines, and dialkyl ketimines. In these cases the asymmetric induction was satisfactorily achieved using beta-silylalkanoyl ketenes and the Evans-Sjögren ketene. C,C-Bis (trimethylsilyl)methylamine ketimines derived from enolizable dialkyl ketones cleanly led to the corresponding C(4) disubstituted beta-lactams without deprotonation. Therefore, a general methodology for a convergent asymmetric synthesis of beta-lactams in which C(4) exists as a quaternary carbon is provided.
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