A Highly Stereocontrolled, One-Pot Approach toward Pyrrolobenzoxazinones and Pyrroloquinazolinones through a Lewis Acid-Catalyzed [3 + 2]-Cycloannulation Process

We report herein a stereocontrolled [3 + 2]-cycloheteroannulation of bis-silyl dienediolate <b>1</b> with 2-aminobenzoic acid- and 2-aminobenzamide-derived imines to furnish highly substituted pyrrolo­[1,2-<i>a</i>]­benzoxazinones <b>3</b> and pyrrolo­[1,2-<i>a</i>]­quinazolinones <b>4</b>, respectively, in good overall yields. This one-pot process rapidly generates molecular complexity and comprises a Lewis acid-catalyzed, vinylogous Mannich reaction of <b>1</b> followed by an intramolecular <i>N</i>,<i>O</i>-acetal- and <i>N</i>,<i>N</i>-aminal formation, respectively, which proceeds with good to excellent stereocontrol