期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 9, 页码 4650-4660出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00535
关键词
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资金
- MINECO
- FEDER [CTQ2012-33664-C02-01, CTQ2012-33664-C02-02]
- UCM-BANCO SANTANDER [GR3/14]
Gold-catalyzed hydroarylation reaction of beta-lactam-tethered allenyl indoles gives azeto-oxepino[4,5-b]-indol-2-ones, tetrahydroazeto-azocino[3,4-b]indol-2-ones, and hexahydroazeto-azepino[3,4-b]indol-2-ones with very high levels of stereo, and regioselectivity, the 7-exo and 8-endo carbocyclization modes by attack of the indole group toward either the internal or the terminal allene carbon, respectively, being favored. Hydroarylation across the central carbon of the allene moiety has not been detected. The controlled gold-catalyzed annulations allowed the formation of fused beta-lactams without harming the sensitive four-membered heterocycle. Besides, a novel gold-catalyzed domino process, namely, the allenic hydroarylation/N1-C4 beta-lactam bond breakage to afford dihydro-oxepino[4,5-b]indole-4-carboxamides, has been discovered.
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