ChemInform Abstract: A Highly Stereocontrolled, One‐Pot Approach Toward Pyrrolobenzoxazinones and Pyrroloquinazolinones Through a Lewis Acid‐Catalyzed [3 + 2]‐Cycloannulation Process.

Abstract

A Highly Stereocontrolled, One-Pot Approach Toward Pyrrolobenzoxazinones and Pyrroloquinazolinones Through a Lewis Acid-Catalyzed [3 + 2]-CycloannulationProcess. -Stereocontrolled cycloheteroannulation of bis-silyl dienediolate (III) with aminobenzoic acid-and aminobenzamide-derived imines provides access to pyrrolobenzoxazinones and pyrroloquinazolinones in good overall yields. This one-pot process generates molecular complexity and proceeds by a Lewis acid-catalyzed, vinylogous Mannich reaction of the bis-silyl dienediolate followed by intramolecular N,O-acetal-or N,N-aminal formation, respectively, which proceeds with good to excellent stereocontrol. -(BOOMHOFF, M.; UKIS, R.; SCHNEIDER*, C.; J. Org. Chem. 80 (2015) 16, 8236-8244, http://dx.doi.org/10.