title: A Highly Stereocontrolled, One-Pot Approach toward Pyrrolobenzoxazinones and Pyrroloquinazolinones through a Lewis Acid-Catalyzed [3 + 2]-Cycloannulation Process.
abstract: We report herein a stereocontrolled [3 + 2]-cycloheteroannulation of bis-silyl dienediolate 1 with 2-aminobenzoic acid- and 2-aminobenzamide-derived imines to furnish highly substituted pyrrolo[1,2-a]benzoxazinones 3 and pyrrolo[1,2-a]quinazolinones 4, respectively, in good overall yields. This one-pot process rapidly generates molecular complexity and comprises a Lewis acid-catalyzed, vinylogous Mannich reaction of 1 followed by an intramolecular N,O-acetal- and N,N-aminal formation, respectively, which proceeds with good to excellent stereocontrol.
authors.affiliation: Institut für Organische Chemie, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Boomhoff
authors.affiliation: Institut für Organische Chemie, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.
authors.forename: Rostyslav
authors.initials: R
authors.lastname: Ukis
authors.affiliation: Institut für Organische Chemie, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.
authors.forename: Christoph
authors.initials: C
authors.lastname: Schneider
mesh_terms: D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D052999:Quinazolinones / Q000138:chemical synthesis* / Q000737:chemistry; D062367:ortho-Aminobenzoates / Q000737:chemistry*
chemical_list: D048588:Benzoxazines; D007097:Imines; D058116:Lewis Acids; D011758:Pyrroles; D052999:Quinazolinones; D062367:ortho-Aminobenzoates; C000219:anthranilamide