Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry **

to related objects

Abstract: Enantioselective reactions are at the core of chemical synthesis. Their development mostly relies on prior knowledge, laborious product analysis and post‐rationalization by theoretical methods. Here, we introduce a simple and fast method to determine enantioselectivities based on mass spectrometry. The method is based on ion mobility separation of diastereomeric intermediates, formed from a chiral catalyst and prochiral reactants, and delayed reactant labeling experiments to link the mass spectra with the reaction kinetics in solution. The data provide rate constants along the reaction paths for the individual diastereomeric intermediates, revealing the origins of enantioselectivity. Using the derived kinetics, the enantioselectivity of the overall reaction can be predicted. Hence, this method can offer a rapid discovery and optimization of enantioselective reactions in the future. We illustrate the method for the addition of cyclopentadiene (CP) to an α,β‐unsaturated aldehyde catalyzed by a diarylprolinol silyl ether.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry ** ; day:03 ; month:06 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (03.06.2022) (gesamt 1)

Creator: Hilgers, Roelant
Yong Teng, Sin
Briš, Anamarija
Pereverzev, Aleksandr Y.
White, Paul
Jansen, Jeroen J.
Roithova, Jana

DOI: 10.1002/anie.202205720

URN: urn:nbn:de:101:1-2022060315415286184656

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

Last update: 15.08.2025, 7:34 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

Hilgers, Roelant
Yong Teng, Sin
Briš, Anamarija
Pereverzev, Aleksandr Y.
White, Paul
Jansen, Jeroen J.
Roithova, Jana

Other Objects (12)

Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry **

Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry **

An enantioselective four-component reaction via assembling two reaction intermediates

An enantioselective four-component reaction via assembling two reaction intermediates

Identifying surface reaction intermediates with photoemission tomography

Identifying surface reaction intermediates with photoemission tomography

Primary Amine Catalyzed Activation of Carbonyl Compounds: A Study on Reaction Pathways and Reactive Intermediates by Mass Spectrometry

Primary Amine Catalyzed Activation of Carbonyl Compounds: A Study on Reaction Pathways and Reactive Intermediates by Mass Spectrometry

Ion mobility spectrometry-tandem mass spectrometry strategies for the on-line monitoring of a continuous microflow reaction

Ion mobility spectrometry-tandem mass spectrometry strategies for the on-line monitoring of a continuous microflow reaction

Structural characterization of reaction intermediates of HECT-mediated ubiquitin transfer

Structural characterization of reaction intermediates of HECT-mediated ubiquitin transfer

Statistical characterization of multiple-reaction monitoring mass spectrometry (MRM-MS) assays for quantitative proteomics

Statistical characterization of multiple-reaction monitoring mass spectrometry (MRM-MS) assays for quantitative proteomics

Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic Maillard Reaction Intermediates

Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic Maillard Reaction Intermediates

Investigation of Reaction Intermediates and Ion Structures in the Gas-Phase

Investigation of Reaction Intermediates and Ion Structures in the Gas-Phase

ADP-Ribosylargininyl reaction of cholix toxin is mediated through diffusible intermediates

ADP-Ribosylargininyl reaction of cholix toxin is mediated through diffusible intermediates

On‐Surface Ullmann‐Type Coupling: Reaction Intermediates and Organometallic Polymer Growth

On‐Surface Ullmann‐Type Coupling: Reaction Intermediates and Organometallic Polymer Growth

Photochemical synthesis of 1,2,4-triazoles via addition reaction of triplet intermediates to diazoalkanes and azomethine ylide intermediates

Photochemical synthesis of 1,2,4-triazoles via addition reaction of triplet intermediates to diazoalkanes and azomethine ylide intermediates

Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry **

Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry **

An enantioselective four-component reaction via assembling two reaction intermediates

An enantioselective four-component reaction via assembling two reaction intermediates

Identifying surface reaction intermediates with photoemission tomography

Identifying surface reaction intermediates with photoemission tomography

Primary Amine Catalyzed Activation of Carbonyl Compounds: A Study on Reaction Pathways and Reactive Intermediates by Mass Spectrometry

Primary Amine Catalyzed Activation of Carbonyl Compounds: A Study on Reaction Pathways and Reactive Intermediates by Mass Spectrometry

Ion mobility spectrometry-tandem mass spectrometry strategies for the on-line monitoring of a continuous microflow reaction

Ion mobility spectrometry-tandem mass spectrometry strategies for the on-line monitoring of a continuous microflow reaction

Structural characterization of reaction intermediates of HECT-mediated ubiquitin transfer

Structural characterization of reaction intermediates of HECT-mediated ubiquitin transfer

Statistical characterization of multiple-reaction monitoring mass spectrometry (MRM-MS) assays for quantitative proteomics

Statistical characterization of multiple-reaction monitoring mass spectrometry (MRM-MS) assays for quantitative proteomics

Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic Maillard Reaction Intermediates

Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic Maillard Reaction Intermediates

Investigation of Reaction Intermediates and Ion Structures in the Gas-Phase

Investigation of Reaction Intermediates and Ion Structures in the Gas-Phase

ADP-Ribosylargininyl reaction of cholix toxin is mediated through diffusible intermediates

ADP-Ribosylargininyl reaction of cholix toxin is mediated through diffusible intermediates

On‐Surface Ullmann‐Type Coupling: Reaction Intermediates and Organometallic Polymer Growth

On‐Surface Ullmann‐Type Coupling: Reaction Intermediates and Organometallic Polymer Growth

Photochemical synthesis of 1,2,4-triazoles via addition reaction of triplet intermediates to diazoalkanes and azomethine ylide intermediates

Photochemical synthesis of 1,2,4-triazoles via addition reaction of triplet intermediates to diazoalkanes and azomethine ylide intermediates

Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry **

Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry **

An enantioselective four-component reaction via assembling two reaction intermediates

An enantioselective four-component reaction via assembling two reaction intermediates

Identifying surface reaction intermediates with photoemission tomography

Identifying surface reaction intermediates with photoemission tomography

Primary Amine Catalyzed Activation of Carbonyl Compounds: A Study on Reaction Pathways and Reactive Intermediates by Mass Spectrometry

Primary Amine Catalyzed Activation of Carbonyl Compounds: A Study on Reaction Pathways and Reactive Intermediates by Mass Spectrometry

Ion mobility spectrometry-tandem mass spectrometry strategies for the on-line monitoring of a continuous microflow reaction

Ion mobility spectrometry-tandem mass spectrometry strategies for the on-line monitoring of a continuous microflow reaction

Structural characterization of reaction intermediates of HECT-mediated ubiquitin transfer

Structural characterization of reaction intermediates of HECT-mediated ubiquitin transfer

Statistical characterization of multiple-reaction monitoring mass spectrometry (MRM-MS) assays for quantitative proteomics

Statistical characterization of multiple-reaction monitoring mass spectrometry (MRM-MS) assays for quantitative proteomics

Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic Maillard Reaction Intermediates

Colorants and Antioxidants Deriving from Methylglyoxal and Heterocyclic Maillard Reaction Intermediates

Investigation of Reaction Intermediates and Ion Structures in the Gas-Phase

Investigation of Reaction Intermediates and Ion Structures in the Gas-Phase

ADP-Ribosylargininyl reaction of cholix toxin is mediated through diffusible intermediates

ADP-Ribosylargininyl reaction of cholix toxin is mediated through diffusible intermediates

On‐Surface Ullmann‐Type Coupling: Reaction Intermediates and Organometallic Polymer Growth

On‐Surface Ullmann‐Type Coupling: Reaction Intermediates and Organometallic Polymer Growth

Photochemical synthesis of 1,2,4-triazoles via addition reaction of triplet intermediates to diazoalkanes and azomethine ylide intermediates

Photochemical synthesis of 1,2,4-triazoles via addition reaction of triplet intermediates to diazoalkanes and azomethine ylide intermediates

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.