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J Org Chem. 2013 Nov 15;78(22):11597-601. doi: 10.1021/jo4019182. Epub 2013 Nov 5.

Inherently chiral iminoresorcinarenes through regioselective unidirectional tautomerization.

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1
Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.

Abstract

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 C4 symmetry. They possess an inherent chirality due to a propeller-like skeleton. For chiral amines, inherently chiral diastereoisomers are observed.

PMID:
24147574
DOI:
10.1021/jo4019182
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