Rh₂(esp)₂-Catalyzed Redox/Cycloaddition Cascade of Diazoaceto­acetate Enones with N-Methyl Nitrones: Diastereoselective Synthesis of β-Lactams with Two Adjacent Chiral Centers

Abstract

A Rh₂(esp)₂-catalyzed diastereoselective synthesis of highly functionalized β-lactams is developed. By employing Rh₂(esp)₂ as the catalyst, a reaction cascade operates by reducing an N-methyl nitrone to the corresponding N-methyl imine in the presence of a first molecule of the diazoacetoacetate enone. A second molecule of the diazoacetoacetate enone sensing a change in the reaction medium undergoes a Wolff rearrangement to afford a vinyl ketene. This vinyl ketene then reacts with the in situ generated N-methyl imine to diastereoselectively furnish a β-lactam with two contiguous stereogenic centers. Extension of this method to the [2+2]-cycloaddition of PMB-protected imines and diazoacetoacetate enones catalyzed by Rh₂(esp)₂ is also reported.

Key words

Rh₂(esp)₂ - diazoacetoacetate enones - N-methyl nitrones - redox - β-lactams

Publication History

Received: 22 November 2021

Accepted after revision: 16 December 2021

Article published online:
01 February 2022

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