Concise Redox Deracemization of Secondary and Tertiary Amines with a Tetrahydroisoquinoline Core via a Nonenzymatic Process.
A concise deracemization of racemic secondary and tertiary amines with a tetrahydroisoquinoline core has been successfully realized by orchestrating a redox process consisted of N-bromosuccinimide oxidation and iridum-catalyzed asymmetric hydrogenation. This compatible redox combination enables one-pot, single-operation deracemization to generate chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines with up to 98% ee in 93% yield, offering a simple and scalable synthetic technique for chiral amines directly from racemic starting materials.
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , Dalian 116023, P. R. China.
Yue
Y
Ji
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , Dalian 116023, P. R. China.|State Key Laboratory of Fine Chemicals, Dalian University of Technology , Dalian 116024, P. R. China.
Lei
L
Shi
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , Dalian 116023, P. R. China.
Mu-Wang
MW
Chen
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , Dalian 116023, P. R. China.
Guang-Shou
GS
Feng
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , Dalian 116023, P. R. China.
Yong-Gui
YG
Zhou
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000737:chemistry*
D000588:Amines; D044005:Tetrahydroisoquinolines