Design, synthesis and application of chiral tetraoxacalix[2]arene[2]triazine‐based organocatalysts in asymmetric Michael addition reactions

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 b...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2019-04, Vol.31 (4), p.293-300
Main Authors: Genc, Hayriye Nevin, Ozgun, Ummu, Sirit, Abdulkadir
Format: Article
Language:English
Subjects:
Adducts
asymmetric synthesis
Catalysis
Michael addition
organocatalysis
stereoselectivity
Tetrahydrofuran
tetraoxacalixarenetriazine
Triazine
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Summary: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).
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.23055