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Rational Synthesis of Multicyclic Bis[2]catenanes
Author(s) -
Bogdan Anca,
Vysotsky Myroslav O.,
Ikai Tomoyuki,
Okamoto Yoshio,
Böhmer Volker
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400195
Subject(s) - catenane , acylation , derivative (finance) , chemistry , metathesis , steric effects , chirality (physics) , stoichiometry , planar chirality , stereochemistry , medicinal chemistry , organic chemistry , polymerization , catalysis , molecule , polymer , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , enantioselective synthesis , financial economics , economics , quark
Bis‐loop tetraurea calix[4]arene 6 has been prepared by acylation of the wide‐rim calix[4]arene tetraamine 1 with the activated bis(urethane) 8 under dilution conditions. Similarly the bis(Boc‐protected) tetraamine 2 is converted into the mono‐loop derivative 3 which after deprotection and acylation gives the bisalkenyl derivative 5 . In apolar solvents this tetraurea calix[4]arene 5 forms regioselectively a single hydrogen‐bonded homodimer, from which the bis[2]catenane 10 a is formed in 49 % by a metathesis reaction followed by hydrogenation. Bis‐loop derivative 6 forms no homodimers for steric reasons, but a stoichiometric mixture with the open‐chain tetraalkenyl derivative 7 a contains exclusively the heterodimer. Metathesis and subsequent hydrogenation now yields 65 % of the pure bis[2]catenane 10 a which could not be isolated from the complex reaction mixture obtained from the homodimer 7 a⋅7 a . The chirality of 10 a ( D 2 symmetry) has been verified by optical resolution using HPLC on a chiral stationary phase.