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Organocatalyzed Highly Diastereo‐ and Enantioselective Tandem Sulfa‐Michael–Mannich Reaction of 2‐Mercaptoquinoline‐3‐carbaldimines with Maleimides
Author(s) -
Wu Lulu,
Wang Youming,
Song Haibin,
Tang Liangfu,
Zhou Zhenghong,
Tang Chuchi
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201300993
Subject(s) - enantioselective synthesis , stereocenter , domino , quinoline , stereoselectivity , yield (engineering) , chemistry , tandem , mannich reaction , organocatalysis , organic chemistry , michael reaction , combinatorial chemistry , cascade reaction , catalysis , materials science , metallurgy , composite material
A highly diastereo‐ and enantioselective organocatalyzed domino sulfa‐Michael–Mannich reaction of 2‐mercaptoquinoline‐3‐carbaldimines with maleimides has been developed. This approach provides a convenient and efficient access to multifuntionalized tetracyclic quinoline derivatives with three contiguous stereocenters in high yield with excellent stereoselectivity (up to >99:1 dr and >99 % ee ).