Journal
ORGANIC LETTERS
Volume 13, Issue 13, Pages 3458-3461Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol201194n
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Funding
- NSFC [20621091, 20672048, 20732002, 20972059]
- 973 program [2010CB833200]
- MOE
- fundamental research funds for the central universities [lzujbky-2010-k09, lzujbky-2009-76, lzujbky-2009-158]
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Regiodivergent annulations of 3-phenoxy alkynyl indoles have been developed and tuned by protective groups through gold catalysis. With electron-donating protective groups, the substrate followed a C3-selective annulation and gave structurally interesting tetrahydro-beta-carboline derivatives possessing potential bioactivity. Using electron-withdrawing protective groups, the substrate underwent a C2-selective annulation and afforded the structurally useful spiro-pseudoindoxyl found in natural indole alkaloids. Notably, an interesting and unusual 1,2-migration of the phenoxy group was found in the C3-selective process.
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