Enantioselective organocatalytic synthesis of quaternary α-amino acids bearing a CF3 Moiety

Ralph Husmann; Erli Sugiono; Stefanie Mersmann; Gerhard Raabe; Magnus Rueping; Carsten Bolm

doi:10.1021/ol103093r

Enantioselective organocatalytic synthesis of quaternary α-amino acids bearing a CF₃ Moiety

Ralph Husmann, Erli Sugiono, Stefanie Mersmann, Gerhard Raabe, Magnus Rueping, Carsten Bolm^*

^*Corresponding author for this work

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

118 Scopus citations

Abstract

A highly enantioselective Friedel-Crafts reaction catalyzed by a chiral phosphoric acid was developed. N-Boc-protected ethyl trifluoropyruvate imine was activated by 6 mol % of catalyst and reacted with a wide variety of indole derivatives to afford quaternary α-amino acids in excellent yields (up to 99%) and high enantioselectivities (up to 98:2 er).(Figure Presented)

Original language	English (US)
Pages (from-to)	1044-1047
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	5
DOIs	https://doi.org/10.1021/ol103093r
State	Published - Mar 4 2011
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol103093r

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abstract = "A highly enantioselective Friedel-Crafts reaction catalyzed by a chiral phosphoric acid was developed. N-Boc-protected ethyl trifluoropyruvate imine was activated by 6 mol % of catalyst and reacted with a wide variety of indole derivatives to afford quaternary α-amino acids in excellent yields (up to 99%) and high enantioselectivities (up to 98:2 er).(Figure Presented)",

author = "Ralph Husmann and Erli Sugiono and Stefanie Mersmann and Gerhard Raabe and Magnus Rueping and Carsten Bolm",

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AU - Husmann, Ralph

AU - Sugiono, Erli

AU - Mersmann, Stefanie

AU - Raabe, Gerhard

AU - Rueping, Magnus

AU - Bolm, Carsten

PY - 2011/3/4

Y1 - 2011/3/4

N2 - A highly enantioselective Friedel-Crafts reaction catalyzed by a chiral phosphoric acid was developed. N-Boc-protected ethyl trifluoropyruvate imine was activated by 6 mol % of catalyst and reacted with a wide variety of indole derivatives to afford quaternary α-amino acids in excellent yields (up to 99%) and high enantioselectivities (up to 98:2 er).(Figure Presented)

AB - A highly enantioselective Friedel-Crafts reaction catalyzed by a chiral phosphoric acid was developed. N-Boc-protected ethyl trifluoropyruvate imine was activated by 6 mol % of catalyst and reacted with a wide variety of indole derivatives to afford quaternary α-amino acids in excellent yields (up to 99%) and high enantioselectivities (up to 98:2 er).(Figure Presented)

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M3 - Article

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JO - Organic Letters

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Enantioselective organocatalytic synthesis of quaternary α-amino acids bearing a CF₃ Moiety

Abstract

ASJC Scopus subject areas

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