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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 ).