Catalytic Diastereo‐ and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen. (16th July 2021)

• Record Type: Journal Article
• Authors: Pan, Hui‐Jie; Lin, Yamei; Gao, Taotao; Lau, Kai Kiat; Feng, Wei; Yang, Binmiao; Zhao, Yu
• Is Part Of: Angewandte Chemie. Volume 133:Number 34(2021)
• Page Start: 18747
• Page End: 18752
• Publication Date: 2021-07-16
• Subjects: chiral diamines -- cooperative catalysis -- double amination of diols -- enantioselectivity -- redox-neutral; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202101517
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: We present herein an unprecedented diastereoconvergent synthesis of vicinal diamines from diols through an economical, redox‐neutral process. Under cooperative ruthenium and Lewis acid catalysis, readily available anilines and 1, 2‐diols (as a mixture of diastereomers) couple to forge two C−N bonds in an efficient and diastereoselective fashion. By identifying an effective chiral iridium/phosphoric acid co‐catalyzed procedure, the first enantioconvergent double amination of racemic 1, 2‐diols has also been achieved, resulting in a practical access to highly valuable enantioenriched vicinal diamines. Abstract : Under cooperative ruthenium and Lewis acid catalysis, readily available anilines and 1, 2‐diols (as a mixture of diastereomers) couple to forge two C−N bonds in an efficient and diastereoselective fashion. By identifying an effective chiral iridium/phosphoric acid co‐catalyzed procedure, enantioconvergent double amination of racemic 1, 2‐diols has also been achieved, resulting in a practical access to highly valuable enantioenriched vicinal diamines.