Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts

Magnus Rueping; Thomas Theissmann; Alexander Kuenkel; René M. Koenigs

doi:10.1002/anie.200802139

Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts

Magnus Rueping^*, Thomas Theissmann, Alexander Kuenkel, René M. Koenigs

^*Corresponding author for this work

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

173 Scopus citations

Abstract

(Chemical Equation Presented) You can count on the counterion in ion-pair intermediates to induce high levels of asymmetry in the title reaction. The efficient transformation proceeds under mild reaction conditions in the presence of an air-stable N-triflylphosphoramide in a low catalyst loading of just 1 mol% to give substituted α-hydroxyesters in good yields and with excellent ee values (see scheme; R = aryl).

Original language	English (US)
Pages (from-to)	6798-6801
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	36
DOIs	https://doi.org/10.1002/anie.200802139
State	Published - Aug 25 2008
Externally published	Yes

Keywords

Asymmetric catalysis
Brønsted acids
Carbonyl-ene reaction
Ion pairs
Organocatalysis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200802139

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abstract = "(Chemical Equation Presented) You can count on the counterion in ion-pair intermediates to induce high levels of asymmetry in the title reaction. The efficient transformation proceeds under mild reaction conditions in the presence of an air-stable N-triflylphosphoramide in a low catalyst loading of just 1 mol% to give substituted α-hydroxyesters in good yields and with excellent ee values (see scheme; R = aryl).",

keywords = "Asymmetric catalysis, Br{\o}nsted acids, Carbonyl-ene reaction, Ion pairs, Organocatalysis",

author = "Magnus Rueping and Thomas Theissmann and Alexander Kuenkel and Koenigs, {Ren{\'e} M.}",

year = "2008",

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doi = "10.1002/anie.200802139",

language = "English (US)",

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T1 - Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts

AU - Rueping, Magnus

AU - Theissmann, Thomas

AU - Kuenkel, Alexander

AU - Koenigs, René M.

PY - 2008/8/25

Y1 - 2008/8/25

N2 - (Chemical Equation Presented) You can count on the counterion in ion-pair intermediates to induce high levels of asymmetry in the title reaction. The efficient transformation proceeds under mild reaction conditions in the presence of an air-stable N-triflylphosphoramide in a low catalyst loading of just 1 mol% to give substituted α-hydroxyesters in good yields and with excellent ee values (see scheme; R = aryl).

AB - (Chemical Equation Presented) You can count on the counterion in ion-pair intermediates to induce high levels of asymmetry in the title reaction. The efficient transformation proceeds under mild reaction conditions in the presence of an air-stable N-triflylphosphoramide in a low catalyst loading of just 1 mol% to give substituted α-hydroxyesters in good yields and with excellent ee values (see scheme; R = aryl).

KW - Asymmetric catalysis

KW - Brønsted acids

KW - Carbonyl-ene reaction

KW - Ion pairs

KW - Organocatalysis

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U2 - 10.1002/anie.200802139

DO - 10.1002/anie.200802139

M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 36

ER -

Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts

Abstract

Keywords

ASJC Scopus subject areas

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