We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Chemo-, Diastereo-, and Enantioselective Iridium-Catalyzed Allylic Intramolecular Dearomatization Reaction of Naphthol Derivatives.
- Authors
Cheng, Qiang; Wang, Ye; You, Shu ‐ Li
- Abstract
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.
- Subjects
NAPHTHOL derivatives; CHEMOSELECTIVITY; ENANTIOSELECTIVE catalysis; NUCLEOPHILIC reactions; CARBON; OXYGEN
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 10, p3557
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201511519