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

作者：Boomhoff Michael; Ukis Rostyslav; Schneider Christoph^*

来源：Journal of Organic Chemistry, 2015, 80(16): 8236-8244.

DOI：10.1021/acs.joc.5b01293

We report herein a stereocontrolled [3 + 2]-cydoheteroaimulation 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.

• 出版日期2015-8-21