Premium
Synthesis of Optically Active 2 H ‐Thiopyrano[2,3‐ b ]quinolines with Three Contiguous Stereocenters via an Organocatalytic Asymmetric Tandem Michael–Henry Reaction
Author(s) -
Wu Lulu,
Wang Youming,
Song Haibin,
Tang Liangfu,
Zhou Zhenghong,
Tang Chuchi
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.201300086
Subject(s) - stereocenter , squaramide , chemistry , bifunctional , tandem , michael reaction , optically active , cascade reaction , enantioselective synthesis , organocatalysis , stereochemistry , catalysis , combinatorial chemistry , organic chemistry , materials science , composite material
Optically active 2 H ‐thiopyrano[2,3‐ b ]quinolines with three contiguous stereocenters have been synthesized via a chiral bifunctional squaramide‐catalyzed tandem Michael–Henry reaction between 2‐mercaptoquinoline‐3‐carbaldehydes and nitroolefins. The reactions proceed with excellent diastereo‐ and enantioselectivity to give the title compounds in high yields with high levels of diastereo‐ and enantioselectivity (up to >99/1 dr and >99% ee , respectively).