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

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

212 Scopus citations

Abstract

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	American English
Journal	Angewandte Chemie International Edition
Volume	44
State	Published - 2005

Disciplines

Chemistry

Keywords

Alkylation
C[BOND]C coupling
Cinchona alkaloids
Enantioselectivity
Nitrogen heterocycles

Cite this

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title = "Highly Enantioselective Organocatalytic Hydroxyalkylation of Indoles with Ethyl Trifluoropyruvate",

abstract = "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[BOND]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",

language = "American English",

volume = "44",

journal = "Angewandte Chemie International Edition",

issn = "1521-3773",

publisher = "John Wiley and Sons Ltd",

}

TY - JOUR

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

Y1 - 2005

N2 - 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 - 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[BOND]C coupling

KW - Cinchona alkaloids

KW - Enantioselectivity

KW - Nitrogen heterocycles

UR - http://dx.doi.org/%2010.1002/anie.200462877

M3 - Article

SN - 1521-3773

VL - 44

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

ER -

Highly Enantioselective Organocatalytic Hydroxyalkylation of Indoles with Ethyl Trifluoropyruvate

Abstract

Disciplines

Keywords

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