BOP-mediated one-pot synthesis of C5-symmetric macrocyclic pyridone pentamers.

We report here, for the first time, the BOP-mediated one-pot macrocyclization that is facilitated and guided by internally placed intramolecular H-bonds to allow for the highly selective formation of five-residue cation-binding macrocycles.

[1]  Z. Du,et al.  One-pot multimolecular macrocyclization for the expedient synthesis of macrocyclic aromatic pentamers by a chain growth mechanism. , 2011, Chemistry, an Asian journal.

[2]  H. Su,et al.  Crystallographic realization of the mathematically predicted densest all-pentagon packing lattice by C5-symmetric "sticky" fluoropentamers. , 2011, Angewandte Chemie.

[3]  H. Su,et al.  Five-fold-symmetric macrocyclic aromatic pentamers: high-affinity cation recognition, ion-pair-induced columnar stacking, and nanofibrillation. , 2011, Journal of the American Chemical Society.

[4]  Hongyu Chen,et al.  Planar macrocyclic fluoropentamers as supramolecular organogelators. , 2011, Organic letters.

[5]  Z. Du,et al.  Computational prediction and experimental verification of pyridine-based helical oligoamides containing four repeating units per helical turn. , 2011, Chemical communications.

[6]  Sam F. Y. Li,et al.  Encapsulation of conventional and unconventional water dimers by water-binding foldamers. , 2011, Organic letters.

[7]  H. Su,et al.  Highly selective one-pot synthesis of H-bonded pentagon-shaped circular aromatic pentamers. , 2011, Chemical communications.

[8]  Y. Liu,et al.  One-pot synthesis of hybrid macrocyclic pentamers with variable functionalizations around the periphery. , 2011, Organic letters.

[9]  M. MacLachlan,et al.  Campestarenes: novel shape-persistent Schiff base macrocycles with 5-fold symmetry. , 2011, Chemical communications.

[10]  Feihe Huang,et al.  Syntheses of copillar[5]arenes by co-oligomerization of different monomers. , 2010, Organic letters.

[11]  H. Su,et al.  Persistently folded circular aromatic amide pentamers containing modularly tunable cation-binding cavities with high ion selectivity. , 2010, Journal of the American Chemical Society.

[12]  H. Su,et al.  Synthesis, structural investigations, hydrogen-deuterium exchange studies, and molecular modeling of conformationally stablilized aromatic oligoamides. , 2010, Journal of the American Chemical Society.

[13]  Quan Gan,et al.  H-bonding directed one-step synthesis of novel macrocyclic peptides from ε-aminoquinolinecarboxylic acid , 2009 .

[14]  J. S. Ferguson,et al.  One-pot formation of large macrocycles with modifiable peripheries and internal cavities. , 2009, Angewandte Chemie.

[15]  B. Gong,et al.  Aromatic oligoamide macrocycles from the bimolecular coupling of folded oligomeric precursors , 2009 .

[16]  H. Su,et al.  Helical organization in foldable aromatic oligoamides by a continuous hydrogen-bonding network. , 2009, Organic letters.

[17]  J. S. Ferguson,et al.  Efficient kinetic macrocyclization. , 2009, Journal of the American Chemical Society.

[18]  L. Sobczyk,et al.  Intramolecular Hydrogen Bonding in o-hydroxy Aryl Schiff Bases , 2009 .

[19]  Zhan-Ting Li,et al.  Hydrogen bonding-directed multicomponent dynamic covalent assembly of mono- and bimacrocycles. Self-sorting and macrocycle exchange. , 2008, The Journal of organic chemistry.

[20]  B. Gong,et al.  Highly conducting transmembrane pores formed by aromatic oligoamide macrocycles. , 2008, Journal of the American Chemical Society.

[21]  H. Su,et al.  Crystallographic evidence of an unusual, pentagon-shaped folding pattern in a circular aromatic pentamer. , 2008, Organic letters.

[22]  J. Leger,et al.  Expanding the registry of aromatic amide foldamers: folding, photochemistry and assembly using diaza-anthracene units. , 2008, The Journal of organic chemistry.

[23]  J. Lehn,et al.  Naphthyridine-based helical foldamers and macrocycles: synthesis, cation binding, and supramolecular assemblies. , 2008, The Journal of organic chemistry.

[24]  Zhan-Ting Li,et al.  Hydrogen-bonded aryl amide macrocycles: synthesis, single-crystal structures, and stacking interactions with fullerenes and coronene. , 2008, The Journal of organic chemistry.

[25]  Kihang Choi,et al.  A Proline-based Macrocyclic Amide with S4 Symmetry , 2008 .

[26]  S. Balasubramanian,et al.  Macrocyclic and helical oligoamides as a new class of G-quadruplex ligands. , 2007, Journal of the American Chemical Society.

[27]  Zhan-Ting Li,et al.  Shape-persistent aromatic amide oligomers: new tools for supramolecular chemistry. , 2006, Chemistry, an Asian journal.

[28]  V. Lynch,et al.  Coordination of oxovanadium(V) in an expanded porphyrin macrocyclet. , 2006, Chemical communications.

[29]  J. Hui,et al.  [6 + 6] Schiff-base macrocycles with 12 imines: giant analogues of cyclohexane. , 2006, Chemical communications.

[30]  Bing Gong,et al.  Aromatic oligoureas: enforced folding and assisted cyclization. , 2006, Organic letters.

[31]  T. Sutherland,et al.  Hydrogen bond directed synthesis of pyridazine and naphthyridine containing macrocycles. , 2005, Chemical communications.

[32]  B. Gong,et al.  Cyclic aromatic oligoamides as highly selective receptors for the guanidinium ion. , 2005, Chemical communications.

[33]  Hua Guo,et al.  Highly efficient, one-step macrocyclizations assisted by the folding and preorganization of precursor oligomers. , 2004, Journal of the American Chemical Society.

[34]  J. Leger,et al.  Strained aromatic oligoamide macrocycles as new molecular clips. , 2004, Organic letters.

[35]  M. MacLachlan,et al.  Ion-induced tubular assembly of conjugated Schiff-base macrocycles. , 2003, Angewandte Chemie.

[36]  B. Gong,et al.  Evolution of Helical Foldamers , 2003 .

[37]  J. Davies.  The cyclization of peptides and depsipeptides , 2003, Journal of peptide science : an official publication of the European Peptide Society.

[38]  C. Hunter,et al.  Directed macrocyclisation reactions , 1994 .