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Design, synthesis and application of chiral tetraoxacalix[2]arene[2]triazine‐based organocatalysts in asymmetric Michael addition reactions
Author(s) -
Genc Hayriye Nevin,
Ozgun Ummu,
Sirit Abdulkadir
Publication year - 2019
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23055
Subject(s) - chemistry , michael reaction , triazine , isobutyraldehyde , adduct , organocatalysis , enantioselective synthesis , tetrahydrofuran , enantiomer , yield (engineering) , catalysis , heteroatom , 1,3,5 triazine , organic chemistry , medicinal chemistry , ring (chemistry) , materials science , solvent , metallurgy
A novel type of oxacalix[2]arene[2]triazine‐based organocatalysts for asymmetric Michael reactions are reported for the first time. Chiral subunits were attached to the heteroatom‐bridged calixaromatic platform by a reaction of ( R )‐ and ( S )‐1‐aminotetraline with tetraoxacalix[2]arene[2]triazine in both enantiomeric forms. To evaluate the catalytic efficiency of the novel organocatalysts, isobutyraldehyde reacted with various substituted and unsubstituted aromatic trans ‐β‐nitrostyrenes in tetrahydrofuran (THF), leading to Michael adducts in excellent yields and enantioselectivites (up to 97% yield and 99% ee).