Asymmetric Brønsted acid catalysis: Enantioselective nucleophilic substitutions and 1,4-additions

Magnus Rueping; Boris J. Nachtsheim; Stefan A. Moreth; Michael Bolte

doi:10.1002/anie.200703668

Asymmetric Brønsted acid catalysis: Enantioselective nucleophilic substitutions and 1,4-additions

Magnus Rueping^*, Boris J. Nachtsheim, Stefan A. Moreth, Michael Bolte

^*Corresponding author for this work

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

335 Scopus citations

Abstract

(Chemical Equation Presented) Executive decision: Depending on the catalyst (both N-triflylphosphoramides), the highly enantioselective Brønsted acid catalyzed addition of indoles to α,β-unsaturated carbonyl compounds provides either α-keto esters (up to 92% ee, left side of the scheme), or a novel type of bisindole (right), which displays atropisomerism. The α-keto esters can also be converted into amino acids by a one-pot 1,4-addition-reductive amination reaction.

Original language	English (US)
Pages (from-to)	593-596
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	3
DOIs	https://doi.org/10.1002/anie.200703668
State	Published - 2008
Externally published	Yes

Keywords

Alkylation
Atropisomers
Michael addition
Nucleophilic substitution
Organocatalysis

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.200703668

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abstract = "(Chemical Equation Presented) Executive decision: Depending on the catalyst (both N-triflylphosphoramides), the highly enantioselective Br{\o}nsted acid catalyzed addition of indoles to α,β-unsaturated carbonyl compounds provides either α-keto esters (up to 92% ee, left side of the scheme), or a novel type of bisindole (right), which displays atropisomerism. The α-keto esters can also be converted into amino acids by a one-pot 1,4-addition-reductive amination reaction.",

keywords = "Alkylation, Atropisomers, Michael addition, Nucleophilic substitution, Organocatalysis",

author = "Magnus Rueping and Nachtsheim, {Boris J.} and Moreth, {Stefan A.} and Michael Bolte",

year = "2008",

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AU - Rueping, Magnus

AU - Nachtsheim, Boris J.

AU - Moreth, Stefan A.

AU - Bolte, Michael

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) Executive decision: Depending on the catalyst (both N-triflylphosphoramides), the highly enantioselective Brønsted acid catalyzed addition of indoles to α,β-unsaturated carbonyl compounds provides either α-keto esters (up to 92% ee, left side of the scheme), or a novel type of bisindole (right), which displays atropisomerism. The α-keto esters can also be converted into amino acids by a one-pot 1,4-addition-reductive amination reaction.

AB - (Chemical Equation Presented) Executive decision: Depending on the catalyst (both N-triflylphosphoramides), the highly enantioselective Brønsted acid catalyzed addition of indoles to α,β-unsaturated carbonyl compounds provides either α-keto esters (up to 92% ee, left side of the scheme), or a novel type of bisindole (right), which displays atropisomerism. The α-keto esters can also be converted into amino acids by a one-pot 1,4-addition-reductive amination reaction.

KW - Alkylation

KW - Atropisomers

KW - Michael addition

KW - Nucleophilic substitution

KW - Organocatalysis

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ER -

Asymmetric Brønsted acid catalysis: Enantioselective nucleophilic substitutions and 1,4-additions

Abstract

Keywords

ASJC Scopus subject areas

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