Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 17, Pages 5282-5285Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201600751
Keywords
asymmetric synthesis; kinetic resolution; multicomponent reaction; organocatalysis; reaction mechanisms
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Funding
- National Natural Science Foundation of China [21320102002, 21502202]
- EPFL (Switzerland)
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Reaction of isonitriles with 3-(arylamino)isobenzofuran-1(3H)-ones in the presence of a catalytic amount of an octahydro (R)-binol-derived chiral phosphoric acid afforded 3-oxo-2-arylisoindoline-1-carboxamides in high yields with good to high enantioselectivities. An enantioselective Ugi four-center three-component reaction of 2-formylbenzoic acids, anilines, and isonitriles was subsequently developed for the synthesis of the same heterocycle. Mechanistic studies indicate that the enantioselectivity results from the dynamic kinetic resolution of the primary Ugi adduct, rather than from the C-C bond-forming process. The resulting heterocycle products are of significant medicinal importance.
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