Asymmetric Hydrogenation of Bis(quinolin‐2‐yl)methanes: A Direct Access to Chiral 1, 3‐Diamines2. Issue 12 (5th October 2018)

• Record Type: Journal Article
• Authors: Li, Bin; Xu, Cong; He, Yan‐Mei; Deng, Guo‐Jun; Fan, Qing‐Hua
• Is Part Of: Chinese journal of chemistry. Volume 36:Issue 12(2018)
• Page Start: 1169
• Page End: 1173
• Publication Date: 2018-10-05
• Subjects: asymmetric catalysis -- hydrogenation -- chiral 1, 3‐diamines -- heterocycles -- ruthenium; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.201800363
• Languages: English
• ISSNs: 1001-604X

Abstract

Abstract: The asymmetric hydrogenation of bis(quinolin‐2‐yl)methanes was described, using chiral cationic ruthenium/monosulfonated diamine complexes to afford chiral bis(tetrahydroquinolin‐2‐yl)methanes in high yield with excellent enantioselectivity and diastereoselectivity. The subsequent transformation of these 1, 3‐diamines to a new class of chiral 6‐membered N ‐heterocyclic carbenes was also developed, which is important but difficult to access. Abstract : The first asymmetric hydrogenation of bis(quinolin‐2‐yl)methanes using chiral cationic ruthenium diamine catalysts was developed with up to > 20 : 1 dr and > 99% ee . This new protocol provides a practical and facile approach to not only chiral 1, 3‐diamines but also a novel class of 6‐membered chiral NHC ligands.