Journal
TETRAHEDRON LETTERS
Volume 56, Issue 32, Pages 4653-4656Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.06.046
Keywords
Asymmetric catalysis; Friedel-Crafts alkylation; Hydrogen bond; Metal-template; Iridium
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Funding
- National Natural Science Foundation of P.R. China [21272192, 21201143, 21472154]
- Program for Changjiang Scholars and Innovative Research Team of P.R. China (PCSIRT)
- National Thousand Talents Program of P.R. China
- 985 Program of the Chemistry and Chemical Engineering disciplines of Xiamen University
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An asymmetric Friedel-Crafts alkylation of indoles with 2-nitro-3-arylacrylates catalyzed by a metal-templated hydrogen bonding catalyst has been established. The asymmetric induction relies on chirality transfer solely from the octahedral metal stereocenter via three weak hydrogen bonds. All the products are provided with good to excellent enantioselectivities while modest diastereoselectivities, which can be converted into a variety of valuable indole-containing chiral building blocks including tryptophan derivatives. (C) 2015 Elsevier Ltd. All rights reserved.
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