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

Dmitry A. Borkin; Shainaz M. Landge; Béla Török

doi:10.1002/chir.20982

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

Dmitry A. Borkin, Shainaz M. Landge, Béla Török

Biochemistry, Chemistry & Physics

University of Massachusetts Boston

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

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.

Original language	English
Pages (from-to)	612-616
Number of pages	5
Journal	Chirality
Volume	23
Issue number	8
DOIs	https://doi.org/10.1002/chir.20982
State	Published - Sep 2011

Scopus Subject Areas

Catalysis
Analytical Chemistry
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

Keywords

Cinchona
chiral trifluoromethylated alcohols
enantioselective
fluoral
indole
organocatalysis

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10.1002/chir.20982

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title = "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.",

keywords = "Cinchona, chiral trifluoromethylated alcohols, enantioselective, fluoral, indole, organocatalysis",

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AU - Borkin, Dmitry A.

AU - Landge, Shainaz M.

AU - Török, Béla

PY - 2011/9

Y1 - 2011/9

N2 - 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.

AB - 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.

KW - Cinchona

KW - chiral trifluoromethylated alcohols

KW - enantioselective

KW - fluoral

KW - indole

KW - organocatalysis

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DO - 10.1002/chir.20982

M3 - Article

SN - 0899-0042

VL - 23

SP - 612

EP - 616

JO - Chirality

JF - Chirality

IS - 8

ER -

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

Abstract

Scopus Subject Areas

Keywords

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