Stereoselective synthesis of six stereoisomers of inherently chiral methoxy-propoxy-butoxy-methoxycarbonylmethoxy-tert-butylcalix[4]arene. Issue 33 (12th August 2015)

• Record Type: Journal Article
• Authors: Polischuk, Kirill A.; Yesypenko, Oleksandr A.; Rozhenko, Alexander B.; Pirozhenko, Vladimir V.; Salimov, Yuriy A.; Ischenko, Valentina V.; Boyko, Vyacheslav I.; Khilya, Volodymyr P.; Kalchenko, Vitaly I.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 33(2015)
• Page Start: 4788
• Page End: 4791
• Publication Date: 2015-08-12
• Subjects: ALUAWXGSUXBBPO-UUVONXHBSA-N -- HAJLKVFESITZJQ-CXOVKITESA-N -- BEEOYRQGCIZFGJ-CXOVKITESA-N -- QXYHFVFADRDSDR-CXOVKITESA-N -- VKUMBDRMBKPKIY-UUVONXHBSA-N -- DHLQUHJOYMHPPS-UUVONXHBSA-N; Calixarenes -- Inherent chirality -- Chiral auxiliary; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.06.055
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: All six possible stereoisomers of calix[4]arenes with four different substituents on the lower rim of the macrocycle have been synthesized by stepwise alkylation of the hydroxyl groups of tert -butylcalix[4]arene using ( R )- or ( S )-1-phenylethylamide groups as chiral auxiliaries. They form three enantiomeric pairs, as confirmed by the values of their specific rotation.