Formal [4+1] annulation of α,α-dialkyl β-oxo amides and dimethylsulfoxonium methylide: a synthetic route to β-hydroxy-γ-lactams?

Chemical Communications Pub Date: 2013-06-26 DOI: 10.1039/C3CC43317J

Abstract

A facile and efficient one-pot synthesis of β-hydroxy-γ-lactams from α,α-dialkyl β-oxo amides and trimethylsulfoxonium iodide in the presence of sodium hydride via a tandem Corey–Chaykovsky reaction and an intramolecular lactamization process is developed.

Graphical abstract: Formal [4+1] annulation of α,α-dialkyl β-oxo amides and dimethylsulfoxonium methylide: a synthetic route to β-hydroxy-γ-lactams
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