Synthesis of Chiral δ‐Aminoboronic Esters by Enantioselective Hydrogenation of 1,2‐Azaborines
Abstract
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 A 1 .
Article Details
Authors (6)
Jiangpeng Liu
Department of Chemistry Boston College 2609 Beacon Street, Merkert Chemistry Center Chestnut Hill MA 02467 USA
Yuping Dai
Université de Pau et des Pays de l’Adour, E2S UPPA / CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254, Hélioparc, 2 avenue P. Angot, 64053 Pau cedex 09, France
Devon Robinson
Department of Chemistry Boston College 2609 Beacon Street, Merkert Chemistry Center Chestnut Hill MA 02467 USA
Bo Li
Karinne Miqueu
Université de Pau et des Pays de l’Adour, E2S UPPA / CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254, Hélioparc, 2 avenue P. Angot, 64053 Pau cedex 09, France
Shih‐Yuan Liu
Department of Chemistry Boston College 2609 Beacon Street, Merkert Chemistry Center Chestnut Hill MA 02467 USA