Volume 64, Issue 24 e202504419
Research Article

Synthesis of Chiral δ-Aminoboronic Esters by Enantioselective Hydrogenation of 1,2-Azaborines

Jiangpeng Liu

Jiangpeng Liu

Department of Chemistry, Boston College, 2609 Beacon Street, Merkert Chemistry Center, Chestnut Hill, MA, 02467 USA

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Yuping Dai

Yuping Dai

E2S UPPA/CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254, Université de Pau et des Pays de l'Adour, Pau Cedex 09, 64053 France

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Devon Robinson

Devon Robinson

Department of Chemistry, Boston College, 2609 Beacon Street, Merkert Chemistry Center, Chestnut Hill, MA, 02467 USA

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Bo Li

Bo Li

Department of Chemistry, Boston College, 2609 Beacon Street, Merkert Chemistry Center, Chestnut Hill, MA, 02467 USA

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Karinne Miqueu

Corresponding Author

Karinne Miqueu

E2S UPPA/CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254, Université de Pau et des Pays de l'Adour, Pau Cedex 09, 64053 France

E-mail: [email protected]; [email protected]

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Shih-Yuan Liu

Corresponding Author

Shih-Yuan Liu

Department of Chemistry, Boston College, 2609 Beacon Street, Merkert Chemistry Center, Chestnut Hill, MA, 02467 USA

E2S UPPA/CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254, Université de Pau et des Pays de l'Adour, Pau Cedex 09, 64053 France

E-mail: [email protected]; [email protected]

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First published: 07 April 2025
Citations: 1

Graphical Abstract

1,2-Azaborines serve as building blocks to enantiomerically enriched δ-aminoboronic esters through the development of the first enantioselective hydrogenation of a boron-containing heteroarene.

Abstract

We describe herein an iridium-catalyzed highly diastereo- and enantioselective hydrogenation of 1,2-azaborines to access δ-aminoboronic esters of potential biological importance. This method represents the first enantioselective hydrogenation of a boron-containing heteroarene and features diverse substitution patterns and wide scope. The synthetic utility of our method was demonstrated by the synthesis of (−)-phenibut and the formal synthesis of (+)-3-PPP and fluvirucinine A1.

Conflict of Interests

The authors declare no conflict of interest.

Data Availability Statement

The data that support the findings of this study are available in the Supporting Information of this article.

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