Stereodivergent Olefination of Enantioenriched Boronic Esters

to related objects

Abstract: A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition‐metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Stereodivergent Olefination of Enantioenriched Boronic Esters ; volume:56 ; number:3 ; year:2017 ; pages:786-790 ; extent:5
Angewandte Chemie / International edition. International edition ; 56, Heft 3 (2017), 786-790 (gesamt 5)

Creator: Armstrong, Roly J.
García‐Ruiz, Cristina
Myers, Eddie L.
Aggarwal, Varinder K.

DOI: 10.1002/anie.201610387

URN: urn:nbn:de:101:1-2022092708013377743207

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

Last update: 15.08.2025, 7:31 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

Armstrong, Roly J.
García‐Ruiz, Cristina
Myers, Eddie L.
Aggarwal, Varinder K.

Other Objects (12)

Stereodivergent Olefination of Enantioenriched Boronic Esters

Stereodivergent Olefination of Enantioenriched Boronic Esters

Synthesis of Boronic Ester γ‐Lactam Building Blocks

Synthesis of Boronic Ester γ‐Lactam Building Blocks

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters

Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters

Ni-Catalyzed Alkyne Cycloaddition to Give Boronic Esters

Ni-Catalyzed Alkyne Cycloaddition to Give Boronic Esters

Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters

Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters

Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations

Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Desymmetrization of C 2 ‐Symmetric Bis (Boronic Esters) by Zweifel Olefinations

Desymmetrization of C 2 ‐Symmetric Bis (Boronic Esters) by Zweifel Olefinations

Fast and efficient copper-mediated 18F-fluorination of arylstannanes, aryl boronic acids, and aryl boronic esters without azeotropic drying

Fast and efficient copper-mediated 18F-fluorination of arylstannanes, aryl boronic acids, and aryl boronic esters without azeotropic drying

Stereodivergent Olefination of Enantioenriched Boronic Esters

Stereodivergent Olefination of Enantioenriched Boronic Esters

Synthesis of Boronic Ester γ‐Lactam Building Blocks

Synthesis of Boronic Ester γ‐Lactam Building Blocks

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters

Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters

Ni-Catalyzed Alkyne Cycloaddition to Give Boronic Esters

Ni-Catalyzed Alkyne Cycloaddition to Give Boronic Esters

Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters

Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters

Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations

Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Desymmetrization of C 2 ‐Symmetric Bis (Boronic Esters) by Zweifel Olefinations

Desymmetrization of C 2 ‐Symmetric Bis (Boronic Esters) by Zweifel Olefinations

Fast and efficient copper-mediated 18F-fluorination of arylstannanes, aryl boronic acids, and aryl boronic esters without azeotropic drying

Fast and efficient copper-mediated 18F-fluorination of arylstannanes, aryl boronic acids, and aryl boronic esters without azeotropic drying

Stereodivergent Olefination of Enantioenriched Boronic Esters

Stereodivergent Olefination of Enantioenriched Boronic Esters

Synthesis of Boronic Ester γ‐Lactam Building Blocks

Synthesis of Boronic Ester γ‐Lactam Building Blocks

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters

Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters

Ni-Catalyzed Alkyne Cycloaddition to Give Boronic Esters

Ni-Catalyzed Alkyne Cycloaddition to Give Boronic Esters

Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters

Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters

Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations

Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Diastereodivergent Synthesis of Cyclopentyl Boronic Esters Bearing Contiguous Fully Substituted Stereocenters

Desymmetrization of C 2 ‐Symmetric Bis (Boronic Esters) by Zweifel Olefinations

Desymmetrization of C 2 ‐Symmetric Bis (Boronic Esters) by Zweifel Olefinations

Fast and efficient copper-mediated 18F-fluorination of arylstannanes, aryl boronic acids, and aryl boronic esters without azeotropic drying

Fast and efficient copper-mediated 18F-fluorination of arylstannanes, aryl boronic acids, and aryl boronic esters without azeotropic drying

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.