Enantioselective Friedel-Crafts Reaction of Indoles with Trifluoroacetaldehyde Catalyzed by Cinchona Alkaloids
Document Type
Article
Publication Date
2011
Publication Title
Chirality
DOI
10.1002/chir.20982
ISSN
1520-636X
Abstract
The first direct asymmetric synthetic preparation of trifluoro-1-(indol-3-yl)ethanols (TFIEs) is described by an enantioselective organocatalytic method from indoles and inexpensive trifluoroacetaldehyde methyl hemiacetal. The reaction is catalyzed by hydroquinine to produce TFIEs in an almost quantitative yield and with enantioselectivities up to 75% at room temperature. The enantioselectivity is strongly dependent on the concentration of substrates and catalyst due to the competitive noncatalyzed reaction. Chirality, 2011. © 2011 Wiley-Liss, Inc.
Recommended Citation
Borkin, Dmitry A., Shainaz M. Landge, Béla Török.
2011.
"Enantioselective Friedel-Crafts Reaction of Indoles with Trifluoroacetaldehyde Catalyzed by Cinchona Alkaloids."
Chirality, 23 (8): 612-616: Wiley.
doi: 10.1002/chir.20982 source: https://onlinelibrary.wiley.com/doi/full/10.1002/chir.20982
https://digitalcommons.georgiasouthern.edu/chem-facpubs/59
