Premium
Synthesis of Spiro[chroman/tetrahydrothiophene‐3,3′‐oxindole] Scaffolds via Heteroatom‐Michael–Michael Reactions: Easily Controlled Enantioselectivity via Bifunctional Catalysts
Author(s) -
Huang Youming,
Zheng Changwu,
Chai Zhuo,
Zhao Gang
Publication year - 2014
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.201300833
Subject(s) - michael reaction , tetrahydrothiophene , chemistry , oxindole , bifunctional , heteroatom , organocatalysis , enantioselective synthesis , catalysis , amine gas treating , organic chemistry , combinatorial chemistry , stereochemistry , ring (chemistry)
An efficient method for the construction of chiral spirooxindole‐chroman and spirooxindole‐tetrahydrothiophene scaffolds with three consecutive chiral centers including an all‐carbon quaternary spirocenter has been developed. This method features an asymmetric thia/oxa‐Michael–Michael cascade sequence in a single operation in the presence of chiral tertiary amine‐thioureas as the catalysts, providing the desired products in good chemical yields and optical purities.