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Enantioselective Organocatalytic Domino Michael/Aldol Reactions: An Efficient Procedure for the Stereocontrolled Construction of 2 H ‐Thiopyrano[2,3‐b]quinoline Scaffolds
Author(s) -
Wu Lulu,
Wang Youming,
Song Haibin,
Tang Liangfu,
Zhou Zhenghong,
Tang Chuchi
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201300450
Subject(s) - domino , aldol reaction , quinoline , enantioselective synthesis , chemistry , michael reaction , organocatalysis , stereochemistry , combinatorial chemistry , catalysis , organic chemistry
An efficient procedure for the stereocontrolled construction of 2 H ‐thiopyrano[2,3‐b]quinoline scaffolds has been developed, starting from simple compounds. The domino Michael/aldol reactions between 2‐mercaptobenzaldehydes and enals, promoted by chiral diphenylprolinol TMS ether, proceed with excellent chemo‐ and enantioselectivity to give the corresponding synthetically useful and pharmaceutically valuable 2 H ‐thiopyrano[2,3‐b]quinolines in high yields with 90–99 % ee .