Highly Stereoselective Synthesis of Isoindole Derivatives Containing an Azetidinone Ring

Abstract

Isoindole derivatives containing an azetidin-2-one moiety were prepared from phthalic anhydride by an approach that involves a [2π+2π] cycloaddition of an imine to a novel ketene generated in situ, and an electrocyclic reaction of a zwitterionic intermediate. The reactions were highly stereoselective and trans-β-lactams were obtained as the sole observed products.

Key words

Schiff bases - isoindoles - polycycles - cycloadditions - ketenes - imines

• References and Notes

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