Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 23
79
Views
1
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Optically Active Aromatic Ether Ketone Macrocycles Containing 2,2′-Dimethoxy-1,1′-binaphthyl-6,6′-diyl Moieties

, , , , &
Pages 4158-4170 | Received 12 Nov 2008, Published online: 29 Oct 2009

REFERENCES

  • (a) Noyori , R. Catalytic asymmetric synthesis . J. Synth. Org. Chem. Jpn. 1992 , 50 , 1131 – 1139 ; (b) Chen , Y. ; Yekta , S. ; Yudin , A. K. Modified BINOL ligands in asymmetric catalysis . Chem. Rev. 2003 , 103 , 3155 – 3212 ; (c) Yamashita , Y. ; Ishitani , H. ; Shimizu , H. ; Kobayashi , S. Highly anti-selective asymmetric aldol reactions using chiral zirconium catalysts: Improvement of activities, structure of the novel zirconium complexes, and effect of a small amount of water for the preparation of the catalysts . J. Am. Chem. Soc. 2002 , 124 , 3292 – 3302 ; (d) Akiyama , T. ; Itoh , J. ; Yokota , K. ; Fuchibe , K. Enantioselective Mannich-type reaction catalyzed by a chiral Br⊘nsted acid . Angew. Chem. Int. Ed. 2004 , 43 , 1566 – 1568 .
  • (a) Cram , D. J. ; Cram , J. M. Host–guest chemistry . Science 1974 , 183 , 803 – 809 ; (b) Kyba , E. P. ; Gokel , G. W. ; Jong , F. ; Koga , K. ; Sousa , L. R. ; Siegel , M. G. ; Kaplan , L. ; Sogah , G. D. Y. ; Cram , D. J. Host–guest complexation, 7: The binaphthyl structural unit in host compounds . J. Org. Chem. 1977 , 42 , 4173 – 4184 ; (c) Collman , J. P. ; Zhang , X. ; Lee , V. J. ; Brauman , J. I. Asymmetric epoxidation catalysed by an ion “binap capped” porphyrin . J. Chem. Soc. Chem. Commun. 1992 , 1647 – 1649 ; (d) Widhalm , M. ; Kalchhauser , H. ; Kählig , K. Synthesis and NMR spectroscopic investigation of a macrocyclic diphosphine ligand and its nickel(II) and palladium(II) complexes . Helv. Chim. Acta 1994 , 77 , 409 – 418 ; (e) Imai , Y. ; Kitazawa , J. ; Sato , T. ; Tajima , N. ; Kuroda , R. ; Matsubara , Y. ; Yoshida , Z. Axial structures of biphenyl compounds linked by diethyl ether chains . Tetrahedron 2007 , 63 , 1995 – 1999 ; (f) Fairfull-Smith , K. ; Redon , P. M. J. ; Haycock , J. W. ; Williams , N. H. Monofunctionalised resorcinarenes . Tetrahedron Lett. 2007 , 48 , 1317 – 1319 .
  • (a) Cao , H. ; Liu , X. ; Ben , T. ; Chen , C. ; Gao , Z. ; Zhang , W. Synthesis and characterization of rigid cyclic oligomer containing thioether moiety. Polym. Prep. 2002, 43, 1112–1113; (b) Dang , G. ; Yang , W. ; Zhao , X. ; Chen , C. ; Li , F. ; Zhang , W. ; Wu , Z. Molecular design and synthesis of a novel aromatic macrocycle with a [1,1′]binaphthalenyl moiety and a p-chlorophenyl substituent. Polym. Prep. 2003, 44, 911; (c) Wang , X. ; Liu , N. ; Cao , H. ; Liu , W. ; Chen , C. ; Zhang , W. ; Wei , Y. Chiral crystal structure of racemic binaphthyl poly(ether ketone) macrocycles. Macromol. Rapid Commun. 2005, 26, 554–557; (d) Liu , N. ; Wang , X. ; Jin , E. ; Chen , C. ; Zhang , W. ; Wei , Y. Synthesis and self-assembly of comb oligomers having rigid racemic or chiral binaphthyl macrocyclic pendant groups. Polymer 2006, 47, 3021–3027; (e) Ema , T. ; Tanida , D. ; Sugita , K. ; Sakai , T. ; Miyazawa , K. ; Ohnishi , A. Chiral selector with multiple hydrogen-bonding sites in a macrocyclic cavity. Org. Lett. 2008, 10, 2365–2368; (f) Srinivas , D. ; Gonnade , R. ; Rajamohanan , P. R. ; Sanjayan , G. J. Pre-organization-mediated macrocylization: Efficient synthesis and structural investigations of BINOL-m-phenylenediamine-derived macrocycles. Tetrahedron Lett. 2008, 49, 2139–2142.
  • (a) Maeda , S. ; Maeyama , K. ; Yonezawa , N. Synthesis of rigid and optically active bis(binaphthyl) cyclic compounds . Synth. Commun. 2007 , 37 , 2663 – 2670 ; (b) Maeyama , K. ; Maeda , S. ; Saito , H. ; Yonezawa , N. Synthesis of wholly aromatic polyketones containing optically active macrocycles . Polym. J. 2007 , 39 , 342 – 346 .
  • Maeyama , K. ; Ogura , K. ; Okamoto , A. ; Sakurai , K. ; Yoshida , Y. ; Ogino , K. ; Yonezawa , N. P2O5-MsOH mediated regioselective diaroylation of 2,2′-dimethoxy-1,1′-binaphthyl . Synth. Commun. 2004 , 34 , 3243 – 3250 .
  • Eaton , P. E. ; Carlson , G. R. ; Lee , G. T. Phosphorus pentoxide–methanesulfonic acid: Convenient alternative to polyphosphoric acid . J. Org. Chem. 1973 , 38 , 4071 – 4073 .
  • (a) Maeyama , K. ; Hikiji , I. ; Ogura , K. ; Okamoto , A. ; Ogino , K. ; Saito , H. ; Yonezawa , N. Synthesis of optically active aromatic poly(ether ketone)s via nucleophilic aromatic substitution polymerization . Polym. J. 2005 , 37 , 707 – 710 ; (b) Maeyama , K. ; Maeda , S. ; Ogino , K. ; Saito , H. ; Yonezawa , N. Synthesis of optically active aromatic poly(ether ketone)s containing 2,2′-bis(4-benzoylphenoxy)-1,1′-binaphthyl-6,6′-ene backbones . React. Funct. Polym. 2005 , 65 , 229 – 237

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.