Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 10, Pages 3496-3499Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201511519
Keywords
aromaticity; asymmetric catalysis; iridium; ligand effects; spiro compounds
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Funding
- National Basic Research Program of China (973 Program) [2015CB856600]
- National Natural Science Foundation of China [21332009, 21421091]
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An iridium-catalyzed intramolecular asymmetric allylic dearomatization reaction of naphthol derivatives is described. Challenges confronted in this reaction include chemoselectivity between carbon and oxygen atoms as nucleophilic centers, diastereoselectivity when contiguous chiral centers are generated, and enantioselective control for constructing an all-carbon quaternary stereocenter. In the presence of an iridium catalyst generated from [{Ir(dbcot)Cl}(2)] (dbcot=dibenzocyclooctatetraene) and a new THQphos (tetrahydroquinolinedinaphthophosphoramidite) ligand, various spironaphthalenones were obtained with up to greater than 95:5 C/O selectivity, greater than 95:5 d.r., and 99% ee, thus providing a general method for the dearomatization of naphthols.
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