Nitrones as Trapping Reagents of alpha,beta-Unsaturated Carbene Intermediates - [1,2]Oxazino[5,4-b]indoles by a Platinum-Catalyzed Intermolecular [3+3] Cycloaddition

作者：Yang Weibo; Wang Tao; Yu Yang; Shi Shuai; Zhang Tuo; Hashmi A Stephen K^*

来源：Advanced Synthesis & Catalysis, 2013, 355(8): 1523-1528.

DOI：10.1002/adsc.201300338

• alkynes
• amines
• indoles
• nitrones
• platinum

Some readily available Boc-protected 2-(3-methoxy-1-propynyl)anilines and nitrones in platinum-catalyzed reactions deliver [1,2]oxazino[5,4-b]indoles. Twelve examples with yields of 4195% are reported. Different substituents like nitro, trifluoromethyl, fluoro, bromo, and ester groups are tolerated. With regard to the mechanism, this reaction probably combines an initial intramolecular cyclization/elimination to vinylcarbenoid species and a subsequent stepwise intermolecular [3+3]cycloaddition with the nitrones.

• 出版日期2013-5