Aryloxide‐Facilitated Catalyst Turnover in Enantioselective α,β‐Unsaturated Acyl Ammonium Catalysis

to related objects

Abstract: A new general concept for α,β‐unsaturated acyl ammonium catalysis is reported that uses p‐nitrophenoxide release from an α,β‐unsaturated p‐nitrophenyl ester substrate to facilitate catalyst turnover. This method was used for the enantioselective isothiourea‐catalyzed Michael addition of nitroalkanes to α,β‐unsaturated p‐nitrophenyl esters in generally good yield and with excellent enantioselectivity (27 examples, up to 79 % yield, 99:1 er). Mechanistic studies identified rapid and reversible catalyst acylation by the α,β‐unsaturated p‐nitrophenyl ester, and a recently reported variable‐time normalization kinetic analysis method was used to delineate the complex reaction kinetics.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Aryloxide‐Facilitated Catalyst Turnover in Enantioselective α,β‐Unsaturated Acyl Ammonium Catalysis ; volume:129 ; number:40 ; year:2017 ; pages:12450-12455 ; extent:6
Angewandte Chemie ; 129, Heft 40 (2017), 12450-12455 (gesamt 6)

Creator: Matviitsuk, Anastassia
Greenhalgh, Mark
Antúnez, Diego‐Javier Barrios
Slawin, Alexandra M. Z.
Smith, Andrew D.

DOI: 10.1002/ange.201706402

URN: urn:nbn:de:101:1-2022091219520113323943

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:20 AM CEST

Data provider

This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.

Show original at data provider

Associated

Matviitsuk, Anastassia
Greenhalgh, Mark
Antúnez, Diego‐Javier Barrios
Slawin, Alexandra M. Z.
Smith, Andrew D.

Other Objects (12)

Aryloxide‐Facilitated Catalyst Turnover in Enantioselective α,β‐Unsaturated Acyl Ammonium Catalysis

Aryloxide‐Facilitated Catalyst Turnover in Enantioselective α,β‐Unsaturated Acyl Ammonium Catalysis

Azaheterocycles based on α,β-unsaturated [alpha beta unsaturated] carbonyls

Azaheterocycles based on α,β-unsaturated [alpha beta unsaturated] carbonyls

Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes

Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes

Selective Catalytic Hydrogenation of α,β-Unsaturated Aldehydes

Selective Catalytic Hydrogenation of α,β-Unsaturated Aldehydes

EPOXIDATION OF α,β-UNSATURATED ESTERS BY DIMETHYLDIOXIRANE

EPOXIDATION OF α,β-UNSATURATED ESTERS BY DIMETHYLDIOXIRANE

Synthesis of Pyrrolidinones via α,β-Unsaturated Acylammonium Ions

Synthesis of Pyrrolidinones via α,β-Unsaturated Acylammonium Ions

Copper-Catalyzed Enantioselective Reduction of α,β-Unsaturated Esters

Copper-Catalyzed Enantioselective Reduction of α,β-Unsaturated Esters

Organocatalytic Asymmetric Epoxidations and Hydroperoxidations of α,β-Unsaturated Ketones

Hochschulschrift

Organocatalytic Asymmetric Epoxidations and Hydroperoxidations of α,β-Unsaturated Ketones

Co (Salox)‐Catalyzed Enantioselective Reduction of α,β‐Unsaturated Esters

Co (Salox)‐Catalyzed Enantioselective Reduction of α,β‐Unsaturated Esters

Chemoselective Reduction of α,β-Unsaturated Aldehydes with AuNPore

Chemoselective Reduction of α,β-Unsaturated Aldehydes with AuNPore

Cyclopropanation of α,β-Unsaturated Aldehydes with a Supported Peptide

Cyclopropanation of α,β-Unsaturated Aldehydes with a Supported Peptide

Efficient whole-cell oxidation of α,β-unsaturated alcohols to α,β-unsaturated aldehydes through the cascade biocatalysis of alcohol dehydrogenase, NADPH oxidase and hemoglobin

Efficient whole-cell oxidation of α,β-unsaturated alcohols to α,β-unsaturated aldehydes through the cascade biocatalysis of alcohol dehydrogenase, NADPH oxidase and hemoglobin

Aryloxide‐Facilitated Catalyst Turnover in Enantioselective α,β‐Unsaturated Acyl Ammonium Catalysis

Aryloxide‐Facilitated Catalyst Turnover in Enantioselective α,β‐Unsaturated Acyl Ammonium Catalysis

Azaheterocycles based on α,β-unsaturated [alpha beta unsaturated] carbonyls

Azaheterocycles based on α,β-unsaturated [alpha beta unsaturated] carbonyls

Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes

Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes

Selective Catalytic Hydrogenation of α,β-Unsaturated Aldehydes

Selective Catalytic Hydrogenation of α,β-Unsaturated Aldehydes

EPOXIDATION OF α,β-UNSATURATED ESTERS BY DIMETHYLDIOXIRANE

EPOXIDATION OF α,β-UNSATURATED ESTERS BY DIMETHYLDIOXIRANE

Synthesis of Pyrrolidinones via α,β-Unsaturated Acylammonium Ions

Synthesis of Pyrrolidinones via α,β-Unsaturated Acylammonium Ions

Copper-Catalyzed Enantioselective Reduction of α,β-Unsaturated Esters

Copper-Catalyzed Enantioselective Reduction of α,β-Unsaturated Esters

Organocatalytic Asymmetric Epoxidations and Hydroperoxidations of α,β-Unsaturated Ketones

Hochschulschrift

Organocatalytic Asymmetric Epoxidations and Hydroperoxidations of α,β-Unsaturated Ketones

Co (Salox)‐Catalyzed Enantioselective Reduction of α,β‐Unsaturated Esters

Co (Salox)‐Catalyzed Enantioselective Reduction of α,β‐Unsaturated Esters

Chemoselective Reduction of α,β-Unsaturated Aldehydes with AuNPore

Chemoselective Reduction of α,β-Unsaturated Aldehydes with AuNPore

Cyclopropanation of α,β-Unsaturated Aldehydes with a Supported Peptide

Cyclopropanation of α,β-Unsaturated Aldehydes with a Supported Peptide

Efficient whole-cell oxidation of α,β-unsaturated alcohols to α,β-unsaturated aldehydes through the cascade biocatalysis of alcohol dehydrogenase, NADPH oxidase and hemoglobin

Efficient whole-cell oxidation of α,β-unsaturated alcohols to α,β-unsaturated aldehydes through the cascade biocatalysis of alcohol dehydrogenase, NADPH oxidase and hemoglobin

Aryloxide‐Facilitated Catalyst Turnover in Enantioselective α,β‐Unsaturated Acyl Ammonium Catalysis

Aryloxide‐Facilitated Catalyst Turnover in Enantioselective α,β‐Unsaturated Acyl Ammonium Catalysis

Azaheterocycles based on α,β-unsaturated [alpha beta unsaturated] carbonyls

Azaheterocycles based on α,β-unsaturated [alpha beta unsaturated] carbonyls

Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes

Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes

Selective Catalytic Hydrogenation of α,β-Unsaturated Aldehydes

Selective Catalytic Hydrogenation of α,β-Unsaturated Aldehydes

EPOXIDATION OF α,β-UNSATURATED ESTERS BY DIMETHYLDIOXIRANE

EPOXIDATION OF α,β-UNSATURATED ESTERS BY DIMETHYLDIOXIRANE

Synthesis of Pyrrolidinones via α,β-Unsaturated Acylammonium Ions

Synthesis of Pyrrolidinones via α,β-Unsaturated Acylammonium Ions

Copper-Catalyzed Enantioselective Reduction of α,β-Unsaturated Esters

Copper-Catalyzed Enantioselective Reduction of α,β-Unsaturated Esters

Organocatalytic Asymmetric Epoxidations and Hydroperoxidations of α,β-Unsaturated Ketones

Hochschulschrift

Organocatalytic Asymmetric Epoxidations and Hydroperoxidations of α,β-Unsaturated Ketones

Co (Salox)‐Catalyzed Enantioselective Reduction of α,β‐Unsaturated Esters

Co (Salox)‐Catalyzed Enantioselective Reduction of α,β‐Unsaturated Esters

Chemoselective Reduction of α,β-Unsaturated Aldehydes with AuNPore

Chemoselective Reduction of α,β-Unsaturated Aldehydes with AuNPore

Cyclopropanation of α,β-Unsaturated Aldehydes with a Supported Peptide

Cyclopropanation of α,β-Unsaturated Aldehydes with a Supported Peptide

Efficient whole-cell oxidation of α,β-unsaturated alcohols to α,β-unsaturated aldehydes through the cascade biocatalysis of alcohol dehydrogenase, NADPH oxidase and hemoglobin

Efficient whole-cell oxidation of α,β-unsaturated alcohols to α,β-unsaturated aldehydes through the cascade biocatalysis of alcohol dehydrogenase, NADPH oxidase and hemoglobin

Cultural heritage institutions wishing to register will find more information here.

Fields marked * need to be filled in.

Username*

Please enter your username

Email*

Please enter your email address

Please do not fill this field

First name

Last name

Password*

Please enter your password

Confirm password*

Please enter the same password

I have read the terms of use and the privacy policy for the collection of personal data and accept them. *

This field is required.

I would like to subscribe to the newsletter of the Deutsche Digitale Bibliothek. See newsletter subscription info.

Account created

Your "My DDB" account has been successfully created. Before you can log in to your account, you must click the confirmation link in the message we just sent to the email address you provided.