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Enantioselective Dearomatization of Naphthol Derivatives with Allylic Alcohols by Cooperative Iridium and Brønsted Acid Catalysis.
- Source :
-
Angewandte Chemie International Edition . 3/13/2017, Vol. 56 Issue 12, p3242-3246. 5p. - Publication Year :
- 2017
-
Abstract
- The combination of a transition-metal catalyst and organocatalyst was designed to achieve a highly enantioselective system for the allylic dearomatization reaction of naphthols with racemic secondary allylic alcohols. The desired β-naphthalenones, bearing an all-carbon quaternary center, were obtained in good yields with high chemo- and enantioselectivities. The cooperative catalytic system, involving a chiral iridium complex and phosphoric acid, provided measurable improvements in yields, and chemo- and enantioselectivities relative to single-catalyst systems. Control experiments indicated that the chiral iridium complex functions as a key species in the control of the absolute configuration, thus enabling the formation of both β-naphthalenone enantiomers by simply employing opposite enantiomeric ligands. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 56
- Issue :
- 12
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 121743823
- Full Text :
- https://doi.org/10.1002/anie.201609693