Title

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

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.