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	American English
Journal	Chirality
Volume	23
DOIs	https://doi.org/10.1002/chir.20982
State	Published - Jan 1 2011

Keywords

Chiral trifluoromethylated alcohols
Cinchona
Enantioselective
Fluoral
Indole
Organocatalysis

DC Disciplines

Chemistry

Access to Document

10.1002/chir.20982License: Unspecified

http://dx.doi.org/10.1002/chir.20982

Cite this

@article{3c17ed2e397f4f979c47c768c47a193a,

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 = "Chiral trifluoromethylated alcohols, Cinchona, Enantioselective, Fluoral, Indole, Organocatalysis",

author = "Borkin, {Dmitry A.} and Landge, {Shainaz M.} and B{\'e}la T{\"o}r{\"o}k",

year = "2011",

month = jan,

day = "1",

doi = "10.1002/chir.20982",

language = "American English",

volume = "23",

journal = "Chirality",

issn = "0899-0042",

publisher = "Wiley-Liss Inc.",

}

TY - JOUR

T1 - Enantioselective Friedel-Crafts Reaction of Indoles with Trifluoroacetaldehyde Catalyzed by Cinchona Alkaloids

AU - Borkin, Dmitry A.

AU - Landge, Shainaz M.

AU - Török, Béla

PY - 2011/1/1

Y1 - 2011/1/1

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 - Chiral trifluoromethylated alcohols

KW - Cinchona

KW - Enantioselective

KW - Fluoral

KW - Indole

KW - Organocatalysis

UR - https://digitalcommons.georgiasouthern.edu/chem-facpubs/59

UR - http://dx.doi.org/10.1002/chir.20982

U2 - 10.1002/chir.20982

DO - 10.1002/chir.20982

M3 - Article

SN - 0899-0042

VL - 23

JO - Chirality

JF - Chirality

ER -

Enantioselective Friedel-Crafts Reaction of Indoles with Trifluoroacetaldehyde Catalyzed by Cinchona Alkaloids

Abstract

Keywords

DC Disciplines

Access to Document

Other files and links

Fingerprint

Cite this