Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 8, Pages 3465-3471Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405245
Keywords
asymmetric synthesis; cascade reactions; organocatalysis; spirooxindole; vinylindoles
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Funding
- National Natural Science Foundation of China [21372002, 21232007]
- PAPD
- Qing Lan Project of Jiangsu Higher Education Institutions
- Graduate Students Foundation of Jiangsu Normal University [2014YZD012]
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The first catalytic asymmetric cascade reaction of 7-vinylindoles has been established by the rational design of such substrates. Cascade reactions with isatin-derived 3-indolylmethanols in the presence of a chiral phosphoric acid derivative allow the diastereo- and enantioselective synthesis of C7-functionalized indoles as well as the construction of cyclopenta[b]indole and spirooxindole frameworks (all > 95: 5 d. r., 94-> 99% ee). This approach not only addresses the great challenge of the catalytic asymmetric synthesis of C7-functionalized indoles, but also provides an efficient method for constructing biologically important cyclopenta[b]indole and spirooxindole scaffolds with excellent optical purity. Investigation of the reaction pathway and activation mode has suggested that this cascade reaction proceeds through a vinylogous Michael addition/Friedel-Crafts process, in which dual H-bonding activation of the two reactants plays a crucial role.
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