An Enantio‐ and Diastereoselective Chemoenzymatic Synthesis of α‐Fluoro β‐Hydroxy Carboxylic Esters

to related objects

Abstract: The trans‐o‐hydroxybenzylidene pyruvate aldolase‐catalysed reactions between fluoropyruvate and many (hetero) aromatic aldehydes yield aldol adducts without subsequent dehydration. Treatment of the reaction products with hydrogen peroxide yields the corresponding syn‐configured α‐fluoro β‐hydroxy carboxylic acids which have >98 % ee. The overall chemoenzymatic approach, in which fluoropyruvate serves as a fluoroacetate equivalent, may be exploited in the synthesis of polar building blocks and fragments with potential value in drug discovery.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: An Enantio‐ and Diastereoselective Chemoenzymatic Synthesis of α‐Fluoro β‐Hydroxy Carboxylic Esters ; volume:128 ; number:23 ; year:2016 ; pages:6879-6882 ; extent:4
Angewandte Chemie ; 128, Heft 23 (2016), 6879-6882 (gesamt 4)

Creator: Howard, James K.
Müller, Marion
Berry, Alan
Nelson, Adam

DOI: 10.1002/ange.201602852

URN: urn:nbn:de:101:1-2022103107201879876604

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

Last update: 15.08.2025, 7:24 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

Howard, James K.
Müller, Marion
Berry, Alan
Nelson, Adam

Other Objects (12)

An Enantio‐ and Diastereoselective Chemoenzymatic Synthesis of α‐Fluoro β‐Hydroxy Carboxylic Esters

Chemoenzymatic Halocyclization of γ,δ‐Unsaturated Carboxylic Acids and Alcohols

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

Chemoenzymatic Oxosulfonylation‐Bioreduction Sequence for the Stereoselective Synthesis of β‐Hydroxy Sulfones

Structural basis for ligand recognition and signaling of hydroxy-carboxylic acid receptor 2

Enzyme-catalyzed synthesis of (S)-cyanohydrins and subsequent hydrolysis to (S)-α-hydroxy-carboxylic acids

Late‐Stage Chemoenzymatic Installation of Hydroxy‐Bearing Allyl Moiety on the Indole Ring of Tryptophan‐Containing Peptides

Diastereoselective [4+4] Cycloadditions

zweidimensionales bewegtes Bild

Carboxylic Acids

Chemo-enzymatic cascade reactions

Chemoenzymatic Synthesis of Sertraline

Synthesis of α,β-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction

An Enantio‐ and Diastereoselective Chemoenzymatic Synthesis of α‐Fluoro β‐Hydroxy Carboxylic Esters

Chemoenzymatic Halocyclization of γ,δ‐Unsaturated Carboxylic Acids and Alcohols

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

Chemoenzymatic Oxosulfonylation‐Bioreduction Sequence for the Stereoselective Synthesis of β‐Hydroxy Sulfones

Structural basis for ligand recognition and signaling of hydroxy-carboxylic acid receptor 2

Enzyme-catalyzed synthesis of (S)-cyanohydrins and subsequent hydrolysis to (S)-α-hydroxy-carboxylic acids

Late‐Stage Chemoenzymatic Installation of Hydroxy‐Bearing Allyl Moiety on the Indole Ring of Tryptophan‐Containing Peptides

Diastereoselective [4+4] Cycloadditions

zweidimensionales bewegtes Bild

Carboxylic Acids

Chemo-enzymatic cascade reactions

Chemoenzymatic Synthesis of Sertraline

Synthesis of α,β-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction

An Enantio‐ and Diastereoselective Chemoenzymatic Synthesis of α‐Fluoro β‐Hydroxy Carboxylic Esters

Chemoenzymatic Halocyclization of γ,δ‐Unsaturated Carboxylic Acids and Alcohols

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

Chemoenzymatic Oxosulfonylation‐Bioreduction Sequence for the Stereoselective Synthesis of β‐Hydroxy Sulfones

Structural basis for ligand recognition and signaling of hydroxy-carboxylic acid receptor 2

Enzyme-catalyzed synthesis of (S)-cyanohydrins and subsequent hydrolysis to (S)-α-hydroxy-carboxylic acids

Late‐Stage Chemoenzymatic Installation of Hydroxy‐Bearing Allyl Moiety on the Indole Ring of Tryptophan‐Containing Peptides

Diastereoselective [4+4] Cycloadditions

zweidimensionales bewegtes Bild

Carboxylic Acids

Chemo-enzymatic cascade reactions

Chemoenzymatic Synthesis of Sertraline

Synthesis of α,β-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction

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.

An Enantio‐ and Diastereoselective Chemoenzymatic Synthesis of α‐Fluoro β‐Hydroxy Carboxylic Esters

Object Details

References and Relationships

Contributors, Places and Time

Further information

Data provider

Associated

Other Objects (12)

An Enantio‐ and Diastereoselective Chemoenzymatic Synthesis of α‐Fluoro β‐Hydroxy Carboxylic Esters

Chemoenzymatic Halocyclization of γ,δ‐Unsaturated Carboxylic Acids and Alcohols

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

Chemoenzymatic Oxosulfonylation‐Bioreduction Sequence for the Stereoselective Synthesis of β‐Hydroxy Sulfones

Structural basis for ligand recognition and signaling of hydroxy-carboxylic acid receptor 2

Enzyme-catalyzed synthesis of (S)-cyanohydrins and subsequent hydrolysis to (S)-α-hydroxy-carboxylic acids

Late‐Stage Chemoenzymatic Installation of Hydroxy‐Bearing Allyl Moiety on the Indole Ring of Tryptophan‐Containing Peptides

Diastereoselective [4+4] Cycloadditions

Carboxylic Acids

Chemo-enzymatic cascade reactions

Chemoenzymatic Synthesis of Sertraline

Synthesis of α,β-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction

An Enantio‐ and Diastereoselective Chemoenzymatic Synthesis of α‐Fluoro β‐Hydroxy Carboxylic Esters

Chemoenzymatic Halocyclization of γ,δ‐Unsaturated Carboxylic Acids and Alcohols

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

Chemoenzymatic Oxosulfonylation‐Bioreduction Sequence for the Stereoselective Synthesis of β‐Hydroxy Sulfones

Structural basis for ligand recognition and signaling of hydroxy-carboxylic acid receptor 2

Enzyme-catalyzed synthesis of (S)-cyanohydrins and subsequent hydrolysis to (S)-α-hydroxy-carboxylic acids

Late‐Stage Chemoenzymatic Installation of Hydroxy‐Bearing Allyl Moiety on the Indole Ring of Tryptophan‐Containing Peptides

Diastereoselective [4+4] Cycloadditions

Carboxylic Acids

Chemo-enzymatic cascade reactions

Chemoenzymatic Synthesis of Sertraline

Synthesis of α,β-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction

An Enantio‐ and Diastereoselective Chemoenzymatic Synthesis of α‐Fluoro β‐Hydroxy Carboxylic Esters

Chemoenzymatic Halocyclization of γ,δ‐Unsaturated Carboxylic Acids and Alcohols

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

Chemoenzymatic Oxosulfonylation‐Bioreduction Sequence for the Stereoselective Synthesis of β‐Hydroxy Sulfones

Structural basis for ligand recognition and signaling of hydroxy-carboxylic acid receptor 2

Enzyme-catalyzed synthesis of (S)-cyanohydrins and subsequent hydrolysis to (S)-α-hydroxy-carboxylic acids

Late‐Stage Chemoenzymatic Installation of Hydroxy‐Bearing Allyl Moiety on the Indole Ring of Tryptophan‐Containing Peptides

Diastereoselective [4+4] Cycloadditions

Carboxylic Acids

Chemo-enzymatic cascade reactions

Chemoenzymatic Synthesis of Sertraline

Synthesis of α,β-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction

Related objects

Reset password