Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 22, Pages 11597-11601Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo4019182
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Funding
- National Science Centre [N N204 187839]
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Tetraformylresorcin[4]arene is obtained in 48% yield via a chromatography-free Duff reaction. The formylated resorcinarene reacts easily with primary aliphatic and aromatic amines. The resulting imines exist exclusively in keto-enamine forms. Owing to a system of intramolecular hydrogen bonds, the reaction selectively leads to regioisomers with C-4 symmetry. They possess an inherent chirality due to a propeller-like skeleton. For chiral amines, inherently chiral diastereoisomers are observed.
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