Asymmetric Synthesis of Tetrahydroquinolines  via  1,5‐Hydride Transfer/Cyclization Catalyzed by Chiral Primary Amine Catalysts | Zendy

Kang Young Ku | Zendy; Kim Dae Young | Zendy

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Asymmetric Synthesis of Tetrahydroquinolines via 1,5‐Hydride Transfer/Cyclization Catalyzed by Chiral Primary Amine Catalysts

Author(s) -

Kang Young Ku,

Kim Dae Young

Publication year - 2013

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201300398

Subject(s) - chemistry , catalysis , amine gas treating , surface modification , hydride , primary (astronomy) , nitrogen atom , combinatorial chemistry , enantioselective synthesis , medicinal chemistry , stereochemistry , organic chemistry , hydrogen , ring (chemistry) , physics , astronomy

Chiral primary amine‐catalyzed asymmetric CH functionalization has been achieved. In this process, enantiotopic C sp 3 H functionalization at the α‐position to the nitrogen atom of 4‐[ ortho ‐(dialkylamino)phenyl]but‐3‐en‐2‐one is activated by chiral 9‐amino(9‐deoxy)‐ epi ‐quinine to afford tetrahydroquinine derivatives with high enantioselectivities (up to 97% ee ).

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