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Inherently chiral calix[4]arenes with asymmetrical superposition of substituents at the lower and the upper rims of macrocycle

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
39
Issue
33
Identifiers
DOI: 10.1016/s0040-4039(98)01246-5

Abstract

Abstract Three types of inherently chiral calix[4]arenes( AAHH BHBH, AHHH HBBH, AAHH HHBH) with asymmetrical superposition of ethyl, diethoxyphosphoryl groups at the lower rim of the macrocycle and bromine atoms at the upper rim, have been synthesized. The key steps of the synthesis are O,O′-phosphorotropic rearrangements of 1,3-distally disubstituted calix[4]arenes into 1,2-proximal isomers, regioselective bromination of the upper rim and hydrolytic removing of phosphoryl or benzoyl group from the lower rim.

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