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Article
Enantioselective Friedel-Crafts Reaction of Indoles with Trifluoroacetaldehyde Catalyzed by Cinchona Alkaloids
Chirality
  • Dmitry A. Borkin
  • Shainaz M. Landge, Georgia Southern University
  • Béla Török, University of Massachusetts Boston
Document Type
Article
Publication Date
1-1-2011
DOI
10.1002/chir.20982
Disciplines
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.

Citation Information
Dmitry A. Borkin, Shainaz M. Landge and Béla Török. "Enantioselective Friedel-Crafts Reaction of Indoles with Trifluoroacetaldehyde Catalyzed by Cinchona Alkaloids" Chirality Vol. 23 Iss. 8 (2011) p. 612 - 616
Available at: http://works.bepress.com/shainaz_landge/32/