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

被引：8
作者：
Genc, Hayriye Nevin [1 ]
Ozgun, Ummu [2 ]
Sirit, Abdulkadir [2 ]
机构：
[1] Necmettin Erbakan Univ, Ahmet Kelesoglu Educ Fac, Dept Sci Educ, TR-42090 Konya, Turkey
[2] Necmettin Erbakan Univ, Ahmet Kelesoglu Educ Fac, Dept Chem, Konya, Turkey
来源：
CHIRALITY | 2019年 / 31卷 / 04期
关键词：
asymmetric synthesis; Michael addition; organocatalysis; stereoselectivity; tetraoxacalix[2]arene[2]triazine; HIGHLY EFFICIENT ORGANOCATALYSTS; CONJUGATE ADDITION; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; PI INTERACTIONS; IONIC LIQUIDS; KETONES; NITROOLEFINS; DERIVATIVES; NITROALKENES; RECOGNITION;
D O I：
10.1002/chir.23055
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
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-beta-nitrostyrenes in tetrahydrofuran (THF), leading to Michael adducts in excellent yields and enantioselectivites (up to 97% yield and 99% ee).
引用
收藏
页码：293 / 300
页数：8
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