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Asymmetric Knoevenagel‐Phospha‐Michael Tandem Reaction Synergistically Catalyzed by Achiral Silanols and Grafted Chiral Amines on Mesoporous Silica
Author(s) -
An Zhe,
Dai Yan,
Jiang Yitao,
He Jing
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900217
Subject(s) - knoevenagel condensation , chemistry , catalysis , bifunctional , enantioselective synthesis , tandem , organocatalysis , michael reaction , yield (engineering) , benzaldehyde , organic chemistry , mesoporous silica , combinatorial chemistry , mesoporous material , materials science , metallurgy , composite material
Highly efficient and enantioselective asymmetric Knoevenagel‐phospha‐Michael tandem reactions have been achieved on bifunctional heterogeneous catalysts with inherent silanols as acidic sites and immobilized chiral amines as basic sites. Final products were afforded in yields of up to 99% and ee values of up to 99%. The effects of substituents on benzaldehyde and molecular dimensions of phosphites have also been investigated. Larger substrates can access the catalytic site inside larger mesoporous pores, thereby improving both of yield and ee of final products.