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Highly Enantioselective SPINOL‐Derived Phosphoric Acid Catalyzed Transfer Hydrogenation of Diverse C=N‐Containing Heterocycles
Author(s) -
Zhang Yiliang,
Zhao Rong,
Bao Robert LiYuan,
Shi Lei
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500330
Subject(s) - enantioselective synthesis , chemistry , phosphoric acid , transfer hydrogenation , catalysis , organic chemistry , aryl , combinatorial chemistry , optically active , diol , alkyl , ruthenium
A highly efficient and enantioselective hydrogenation of diversely substituted C=N‐containing heterocyclic compounds such as 3‐aryl‐1,4‐benzoxazines and 2‐arylquinolines was experimentally explored by using 1,1′‐spirobiindane‐7,7′‐diol‐derived chiral phosphoric acids as the catalyst. This method provides straightforward access to the corresponding tetrahydroquinolines and dihydro‐2 H ‐1,4‐benzothiazines in high yields (85–99 %) with excellent enantioselectivities (91–99 %). The attractive features of this procedure, which include mild reaction conditions, operational simplicity, relatively low catalyst loading (1 mol‐%), and high levels of enantioselectivities, make it a useful approach for the practical synthesis of optically active nitrogen‐containing aromatic heterocycles.