Synthesis 2011(13): 2054-2061  
DOI: 10.1055/s-0030-1260608
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Short Domino Sequence to Dioxa[4.3.3]propellanes

Joaquin Barjaua, Gregor Schnakenburgb, Siegfried R. Waldvogel*a
a Institute for Organic Chemistry, University of Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
Fax: +49(6131)3926777; e-Mail: waldvogel@uni-mainz.de;
b X-ray Analysis Department, Institute for Inorganic Chemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Further Information

Publication History

Received 22 February 2011
Publication Date:
26 May 2011 (online)

Abstract

A variety of dioxa[4.3.3]propellanes are efficiently obtained starting from a dehydrotetramer of 2,4-dimethylphenol. The final installation of the phenol component requires a domino sequence based on electrophilic substitution and a ketalization process. The molecular structure of these dioxa[4.3.3]propellanes was elucidated by 2D NMR techniques as well as X-ray analysis of suitable single crystals. Most of these polycyclic products were formed with high regio- and diastereoselectivity.

    References

  • 1 Weber RW. Cook JM. Can. J. Chem.  1977,  56:  189 
  • 2a Konishi M. Ohkuma H. Tsuno T. Oki T. J. Am. Chem. Soc.  1990,  112:  3715 
  • 2b Ellestad GA. Kunstmann MP. Whaley HA. Patterson EL. J. Am. Chem. Soc.  1968,  90:  1325 
  • 2c Qian-Cutrone J. Gao Q. Huang S. Klohr SE. Veitch JA. Shu Y.-Z. J. Nat. Prod.  1994,  57:  1656 
  • 3a Kaszynski P. Michl J. J. Am. Chem. Soc.  1988,  110:  5225 
  • 3b Wiberg KB. Burgmaier GJ. J. Am. Chem. Soc.  1972,  94:  7396 
  • 4a Snatze G. Zanati G. Justus Liebigs Ann.  1965,  684:  62 
  • 4b Nerdel F. Janowsky K. Frank D. Tetrahedron Lett.  1965,  6:  2979 
  • 5 For a complete review in recent propellane synthesis, see: Ainoliisa JP. Ari MPK. Tetrahedron  2005,  61:  8769 
  • 6 Nicolaou KC. Snyder SA. Montagnon T. Vassilikogiannakis G. Angew. Chem. Int. Ed.  2002,  41:  1668 
  • 7 Trost BM. Shi Y. J. Am. Chem. Soc.  1991,  113:  701 
  • 8 Asahi K. Nishino H. Tetrahedron  2008,  64:  1620 
  • 9a Jamrozik J. Jamrozik M. Sciborowicz P. Zeslawski W. Monatsh. Chem.  1995,  126:  587 
  • 9b Weniges K. Guenther P. Kasel W. Hubertus G. Günther P. Angew. Chem. Int. Ed.  1981,  20:  960 
  • 9c Ginsburg D. Top. Curr. Chem.  1987,  137:  1 
  • For recent reviews, see:
  • 10a Waldvogel SR. Pure Appl. Chem.  2010,  82:  1055 
  • 10b Yoshida J.-I. Kataoka K. Horcajada R. Nagaki A. Chem. Rev.  2008,  108:  2265 
  • 10c Sperry JB. Wright DL. Chem. Soc. Rev.  2006,  35:  605 
  • 10d Little RD. Moeller KD. Electrochem. Soc. Interface  2002,  11:  28 
  • 10e Moeller KD. Tetrahedron  2000,  56:  9527 
  • For selected recent examples, see:
  • 10f Kirste A. Schnakenburg G. Stecker F. Fischer A. Waldvogel SR. Angew. Chem. Int. Ed.  2010,  49:  971 
  • 10g Xu H.-C. Brandt JD. Moeller KD. Tetrahedron Lett.  2008,  49:  3868 
  • 10h Tang F. Chen C. Moeller KD. Synthesis  2007,  3411 
  • 10i Wu H. Moeller KD. Org. Lett.  2007,  9:  4599 
  • 10j Malkowsky IM. Griesbach U. Pütter H. Waldvogel SR. Eur. J. Org. Chem.  2006,  4569 
  • 10k Malkowsky IM. Rommel CE. Fröhlich R. Griesbach U. Pütter H. Waldvogel SR. Chem. Eur. J.  2006,  12:  7482 
  • 10l Miller AK. Hughes CC. Kennedy-Smith JJ. Gradl SN. Trauner D. J. Am. Chem. Soc.  2006,  128:  17057 
  • 10m Hughes CC. Miller AK. Trauner D. Org. Lett.  2005,  7:  3425 
  • 10n Sperry JB. Wright DL. J. Am. Chem. Soc.  2005,  127:  8034 
  • 10o Girard N. Hurvois J.-P. Moinet C. Toupet L. Eur. J. Org. Chem.  2005,  2269 
  • 10p Liu B. Duan S. Sutterer AC. Moeller KD. J. Am. Chem. Soc.  2002,  124:  10101 
  • 11a Hoshino O. In The Alkaloids   Vol. 51:  Cordell GA. Academic Press; New York: 1998.  p.323 
  • 11b Martin SF. In The Alkaloids   Vol. 30:  Brossi A. Academic Press; New York: 1987.  p.251 
  • 11c Cave JM. Scrowston RM. Heterocycles  1994,  2:  1083 
  • 11d Mori K. Takahashi M. Yamamura S. Nishiyama S. Tetrahedron  2001,  57:  5527 
  • 12 Malkowsky IM. Rommel CE. Wedeking K. Fröhlich R. Bergander K. Nieger M. Quaiser C. Griesbach U. Pütter H. Waldvogel SR. Eur. J. Org. Chem.  2006,  241 
  • 13 Barjau J. Schnakenburg G. Waldvogel SR. Angew. Chem. Int. Ed.  2011,  50:  1415 
  • 14a Collins CJ. Q. Rev., Chem. Soc.  1960,  14:  357 
  • 14b Coveney DJ. In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Fleming I. Pergamon; Oxford: 1991.  p.721 
  • 15 Barjau J. Königs P. Waldvogel SR. Synlett  2008,  2309 
  • 17a Clayden J. Greeves N. Warren S. Wothers P. Organic Chemistry   Oxford University Press; Oxford: 2001. 
  • 17b Knecht E. J. Chem. Soc., Trans.  1924,  125:  1537 
  • 17c Miller B. Saidi MR. J. Am. Chem. Soc.  1976,  98:  2227 
  • 17d Khanna RN. Singh KP. Sharma J. Org. Prep. Proced. Int.  1992,  6:  687 
  • 18 Perrin DD. Armarego WLF. In Purification of Laboratory Chemicals   3rd ed.:  Butterworth-Heinemann Ltd; Oxford: 1988. 
16

Between -10 and -78 ˚C.

19

Seebach’s reagent: a mixture of phosphomolybdic acid (25 g), cerium(IV) sulfate (7.5 g), H2O (500 mL), and concd H2SO4 (25 mL).