Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 34, Pages 11004-11008Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804330
Keywords
chiral phosphoric acids; enantioselectivity; heterocycles; indoles; organocatalysis
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Funding
- National 1000 Talent Plan of China
- Tianjin University
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The direct enantioselective 1,4- and 1,8-arylations of 7-methide-7H-indoles and 6-methide-6H-indoles, respectively, generated in situ from diarylmethanols, with electron-rich arenes as nucleophiles, has been achieved in the presence of chiral phosphoric acids (CPAs). These two remote activation protocols provide an efficient approach for the construction of diverse hetero-triarylmethanes in high yields (up to 97%) and with excellent enantioselectivities (up to 96%). Mechanistically inspired experiments tentatively indicate that the catalytic enantioselective 1,4-addition as well as the formal S(N)1 substitution could proceed efficiently in the similar catalytic systems. Furthermore, the modification of the catalytic system and diarylmethanol structure successfully deviates the reactivity toward a remote, highly enantioselective 1,8-arylation reaction. This flexible activation mode and novel reactivity of diarylmethanols expand the synthetic potential of chiral phosphoric acids.
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