Highly enantioselective organocatalytic hydroxyalkylation of indoles with ethyl trifluoropyruvate

Béla Török; Abid Shaikh; Gábor London; Joseph Esquibel; Marianna Török; Shilpa C. Mhadgut; Ping Yan; G. K. S. Prakash

doi:10.1002/anie.200462877

Highly enantioselective organocatalytic hydroxyalkylation of indoles with ethyl trifluoropyruvate

Béla Török
, Abid Shaikh
, Gábor London
, Joseph Esquibel
, Marianna Török
, Shilpa C. Mhadgut
, Ping Yan
, G. K. S. Prakash

Biochemistry, Chemistry & Physics

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

217 Scopus citations

Abstract

(Chemical Equation Presented) Readily available cinchona alkaloids have been used as organocatalysts in the highly efficient stereoselective hydroxyalkylation of heteroaromatics such as indoles with 3,3,3- trifluoropyruvate (2, see scheme). High yields and ee values of both enantiomers of the products, depending on the catalyst used, indicate the usefulness of the developed methodology.

Original language	English
Pages (from-to)	3086-3089
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	44
Issue number	20
DOIs	https://doi.org/10.1002/anie.200462877
State	Published - May 13 2005

Scopus Subject Areas

Catalysis
General Chemistry

Keywords

Alkylation
C-C coupling
Cinchona alkaloids
Enantioselectivity
Nitrogen heterocycles

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10.1002/anie.200462877

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title = "Highly enantioselective organocatalytic hydroxyalkylation of indoles with ethyl trifluoropyruvate",

abstract = "(Chemical Equation Presented) Readily available cinchona alkaloids have been used as organocatalysts in the highly efficient stereoselective hydroxyalkylation of heteroaromatics such as indoles with 3,3,3- trifluoropyruvate (2, see scheme). High yields and ee values of both enantiomers of the products, depending on the catalyst used, indicate the usefulness of the developed methodology.",

keywords = "Alkylation, C-C coupling, Cinchona alkaloids, Enantioselectivity, Nitrogen heterocycles",

author = "B{\'e}la T{\"o}r{\"o}k and Abid Shaikh and G{\'a}bor London and Joseph Esquibel and Marianna T{\"o}r{\"o}k and Mhadgut, \{Shilpa C.\} and Ping Yan and Prakash, \{G. K. S.\}",

year = "2005",

month = may,

day = "13",

doi = "10.1002/anie.200462877",

language = "English",

volume = "44",

pages = "3086--3089",

journal = "Angewandte Chemie International Edition",

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T1 - Highly enantioselective organocatalytic hydroxyalkylation of indoles with ethyl trifluoropyruvate

AU - Török, Béla

AU - Shaikh, Abid

AU - London, Gábor

AU - Esquibel, Joseph

AU - Török, Marianna

AU - Mhadgut, Shilpa C.

AU - Yan, Ping

AU - Prakash, G. K. S.

PY - 2005/5/13

Y1 - 2005/5/13

N2 - (Chemical Equation Presented) Readily available cinchona alkaloids have been used as organocatalysts in the highly efficient stereoselective hydroxyalkylation of heteroaromatics such as indoles with 3,3,3- trifluoropyruvate (2, see scheme). High yields and ee values of both enantiomers of the products, depending on the catalyst used, indicate the usefulness of the developed methodology.

AB - (Chemical Equation Presented) Readily available cinchona alkaloids have been used as organocatalysts in the highly efficient stereoselective hydroxyalkylation of heteroaromatics such as indoles with 3,3,3- trifluoropyruvate (2, see scheme). High yields and ee values of both enantiomers of the products, depending on the catalyst used, indicate the usefulness of the developed methodology.

KW - Alkylation

KW - C-C coupling

KW - Cinchona alkaloids

KW - Enantioselectivity

KW - Nitrogen heterocycles

UR - https://www.scopus.com/pages/publications/18844380223

U2 - 10.1002/anie.200462877

DO - 10.1002/anie.200462877

M3 - Article

SN - 1521-3773

VL - 44

SP - 3086

EP - 3089

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 20

ER -

Highly enantioselective organocatalytic hydroxyalkylation of indoles with ethyl trifluoropyruvate

Abstract

Scopus Subject Areas

Keywords

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