Synthesis of Chiral δ‐Aminoboronic Esters by Enantioselective Hydrogenation of 1,2‐Azaborines
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 A<sub>1</sub>.
Authors
- Jiangpeng Liu
- Shih‐Yuan Liu (ORCID: https://orcid.org/0000-0003-3148-9147)
- Bo Li (ORCID: https://orcid.org/0000-0002-3726-2640)
- Karinne Miqueu
- Devon Robinson
- Yuping Dai
Institutions
- Boston College (US)
- Centre National de la Recherche Scientifique (FR)
- Université de Pau et des Pays de l'Adour (FR)
- Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux (FR)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2025-04-07
- DOI
- https://doi.org/10.1002/anie.202504419
- Citations
- 2
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 1.07
Funders
- National Science Foundation
- Boston College
- Université de Pau et des Pays de l'Adour
- National Institutes of Health
- National Institute of General Medical Sciences
- Division of Chemistry