Enantiospecific Synthesis of 1,3‐Disubstituted Allenes from Propargylic Carbonates through a Borylation‐1,2‐Elimination Process

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Abstract: An array of enantioenriched vinyl boronates bearing an allylic carbonate moiety have been prepared through selective hydroboration of propargyl carbonates. Treatment of these vinyl boronates with TBAF in THF affords enantioenriched 1,3‐disubstituted allenes through a novel 1,2‐anti elimination in good yields and high enantiospecificities.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Enantiospecific Synthesis of 1,3‐Disubstituted Allenes from Propargylic Carbonates through a Borylation‐1,2‐Elimination Process ; day:23 ; month:11 ; year:2023 ; extent:7
Advanced synthesis & catalysis ; (23.11.2023) (gesamt 7)

Creator: Jarava‐Barrera, Carlos
Parra, Alejandro
Quesada, Sergio
Orgaz‐Gordillo, Sergio
Fernández de la Pradilla, Roberto
Viso, Alma
Teresa, Javier
Alonso, Inés
Tortosa, Mariola

DOI: 10.1002/adsc.202300813

URN: urn:nbn:de:101:1-2023112414272761808315

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

Last update: 15.08.2025, 7:34 AM CEST

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Associated

Jarava‐Barrera, Carlos
Parra, Alejandro
Quesada, Sergio
Orgaz‐Gordillo, Sergio
Fernández de la Pradilla, Roberto
Viso, Alma
Teresa, Javier
Alonso, Inés
Tortosa, Mariola

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Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

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Enantiospecific Synthesis of 1,3‐Disubstituted Allenes from Propargylic Carbonates through a Borylation‐1,2‐Elimination Process

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Other Objects (12)

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Chirality Transfer in Gold (I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes

Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Stereoselectivity control in Rh-catalyzed β-OH elimination for chiral allene formation

Miyaura Borylation Reaction

Krankensammelstelle Allenes

Allene chemistry

Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C2‐Symmetric Bis(phosphine) Ligands

Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C 2 ‐Symmetric Bis (phosphine) Ligands

Synthese und Reaktionen cryptochiraler Allene sowie die Herstellung fluorhaltiger Allene

Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes

Chirality Transfer in Gold (I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes

Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

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Stereoselectivity control in Rh-catalyzed β-OH elimination for chiral allene formation

Miyaura Borylation Reaction

Krankensammelstelle Allenes

Allene chemistry

Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C2‐Symmetric Bis(phosphine) Ligands

Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C 2 ‐Symmetric Bis (phosphine) Ligands

Synthese und Reaktionen cryptochiraler Allene sowie die Herstellung fluorhaltiger Allene

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Chirality Transfer in Gold (I)‐Catalysed Hydroalkoxylation of 1,3‐Disubstituted Allenes

Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow‐Generated Diazo Compounds and Propargylated Amines

Stereoselectivity control in Rh-catalyzed β-OH elimination for chiral allene formation

Miyaura Borylation Reaction

Krankensammelstelle Allenes

Allene chemistry

Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C2‐Symmetric Bis(phosphine) Ligands

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Synthese und Reaktionen cryptochiraler Allene sowie die Herstellung fluorhaltiger Allene

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