Enantioselective Friedel-Crafts reaction of indoles with trifluoroacetaldehyde catalyzed by Cinchona alkaloids.

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.

journal_name

Chirality

journal_title

Chirality

authors

Borkin DA,Landge SM,Török B

doi

10.1002/chir.20982

subject

Has Abstract

pub_date

2011-09-01 00:00:00

pages

612-6

issue

8

eissn

0899-0042

issn

1520-636X

journal_volume

23

pub_type

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