Short Domino Sequence to Dioxa[4.3.3]propellanes

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.

propellanes - phenols - polycycles - domino reaction - regioselectivity

References

<A NAME="RT21711SS-1">1</A> Weber RW. Cook JM. Can. J. Chem.  1977,  56:  189 

<A NAME="RT21711SS-2A">2a</A> Konishi M. Ohkuma H. Tsuno T. Oki T. J. Am. Chem. Soc.  1990,  112:  3715 

<A NAME="RT21711SS-2B">2b</A> Ellestad GA. Kunstmann MP. Whaley HA. Patterson EL. J. Am. Chem. Soc.  1968,  90:  1325 

<A NAME="RT21711SS-2C">2c</A> Qian-Cutrone J. Gao Q. Huang S. Klohr SE. Veitch JA. Shu Y.-Z. J. Nat. Prod.  1994,  57:  1656 

<A NAME="RT21711SS-3A">3a</A> Kaszynski P. Michl J. J. Am. Chem. Soc.  1988,  110:  5225 

<A NAME="RT21711SS-3B">3b</A> Wiberg KB. Burgmaier GJ. J. Am. Chem. Soc.  1972,  94:  7396 

<A NAME="RT21711SS-4A">4a</A> Snatze G. Zanati G. Justus Liebigs Ann.  1965,  684:  62 

<A NAME="RT21711SS-4B">4b</A> Nerdel F. Janowsky K. Frank D. Tetrahedron Lett.  1965,  6:  2979 

<A NAME="RT21711SS-5">5</A> For a complete review in recent propellane synthesis, see: Ainoliisa JP. Ari MPK. Tetrahedron  2005,  61:  8769 

<A NAME="RT21711SS-6">6</A> Nicolaou KC. Snyder SA. Montagnon T. Vassilikogiannakis G. Angew. Chem. Int. Ed.  2002,  41:  1668 

<A NAME="RT21711SS-7">7</A> Trost BM. Shi Y. J. Am. Chem. Soc.  1991,  113:  701 

<A NAME="RT21711SS-8">8</A> Asahi K. Nishino H. Tetrahedron  2008,  64:  1620 

<A NAME="RT21711SS-9A">9a</A> Jamrozik J. Jamrozik M. Sciborowicz P. Zeslawski W. Monatsh. Chem.  1995,  126:  587 

<A NAME="RT21711SS-9B">9b</A> Weniges K. Guenther P. Kasel W. Hubertus G. Günther P. Angew. Chem. Int. Ed.  1981,  20:  960 

<A NAME="RT21711SS-9C">9c</A> Ginsburg D. Top. Curr. Chem.  1987,  137:  1 

For recent reviews, see:

<A NAME="RT21711SS-10A">10a</A> Waldvogel SR. Pure Appl. Chem.  2010,  82:  1055 

<A NAME="RT21711SS-10B">10b</A> Yoshida J.-I. Kataoka K. Horcajada R. Nagaki A. Chem. Rev.  2008,  108:  2265 

<A NAME="RT21711SS-10C">10c</A> Sperry JB. Wright DL. Chem. Soc. Rev.  2006,  35:  605 

<A NAME="RT21711SS-10D">10d</A> Little RD. Moeller KD. Electrochem. Soc. Interface  2002,  11:  28 

<A NAME="RT21711SS-10E">10e</A> Moeller KD. Tetrahedron  2000,  56:  9527 

For selected recent examples, see:

<A NAME="RT21711SS-10F">10f</A> Kirste A. Schnakenburg G. Stecker F. Fischer A. Waldvogel SR. Angew. Chem. Int. Ed.  2010,  49:  971 

<A NAME="RT21711SS-10G">10g</A> Xu H.-C. Brandt JD. Moeller KD. Tetrahedron Lett.  2008,  49:  3868 

<A NAME="RT21711SS-10H">10h</A> Tang F. Chen C. Moeller KD. Synthesis  2007,  3411 

<A NAME="RT21711SS-10I">10i</A> Wu H. Moeller KD. Org. Lett.  2007,  9:  4599 

<A NAME="RT21711SS-10J">10j</A> Malkowsky IM. Griesbach U. Pütter H. Waldvogel SR. Eur. J. Org. Chem.  2006,  4569 

<A NAME="RT21711SS-10K">10k</A> Malkowsky IM. Rommel CE. Fröhlich R. Griesbach U. Pütter H. Waldvogel SR. Chem. Eur. J.  2006,  12:  7482 

<A NAME="RT21711SS-10L">10l</A> Miller AK. Hughes CC. Kennedy-Smith JJ. Gradl SN. Trauner D. J. Am. Chem. Soc.  2006,  128:  17057 

<A NAME="RT21711SS-10M">10m</A> Hughes CC. Miller AK. Trauner D. Org. Lett.  2005,  7:  3425 

<A NAME="RT21711SS-10N">10n</A> Sperry JB. Wright DL. J. Am. Chem. Soc.  2005,  127:  8034 

<A NAME="RT21711SS-10O">10o</A> Girard N. Hurvois J.-P. Moinet C. Toupet L. Eur. J. Org. Chem.  2005,  2269 

<A NAME="RT21711SS-10P">10p</A> Liu B. Duan S. Sutterer AC. Moeller KD. J. Am. Chem. Soc.  2002,  124:  10101 

<A NAME="RT21711SS-11A">11a</A> Hoshino O. In The Alkaloids   Vol. 51:  Cordell GA. Academic Press; New York: 1998.  p.323 

<A NAME="RT21711SS-11B">11b</A> Martin SF. In The Alkaloids   Vol. 30:  Brossi A. Academic Press; New York: 1987.  p.251 

<A NAME="RT21711SS-11C">11c</A> Cave JM. Scrowston RM. Heterocycles  1994,  2:  1083 

<A NAME="RT21711SS-11D">11d</A> Mori K. Takahashi M. Yamamura S. Nishiyama S. Tetrahedron  2001,  57:  5527 

<A NAME="RT21711SS-12">12</A> 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 

<A NAME="RT21711SS-13">13</A> Barjau J. Schnakenburg G. Waldvogel SR. Angew. Chem. Int. Ed.  2011,  50:  1415 

<A NAME="RT21711SS-14A">14a</A> Collins CJ. Q. Rev., Chem. Soc.  1960,  14:  357 

<A NAME="RT21711SS-14B">14b</A> Coveney DJ. In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Fleming I. Pergamon; Oxford: 1991.  p.721 

<A NAME="RT21711SS-15">15</A> Barjau J. Königs P. Waldvogel SR. Synlett  2008,  2309 

<A NAME="RT21711SS-16">16</A>

Between -10 and -78 ˚C.

<A NAME="RT21711SS-17A">17a</A> Clayden J. Greeves N. Warren S. Wothers P. Organic Chemistry   Oxford University Press; Oxford: 2001. 

<A NAME="RT21711SS-17B">17b</A> Knecht E. J. Chem. Soc., Trans.  1924,  125:  1537 

<A NAME="RT21711SS-17C">17c</A> Miller B. Saidi MR. J. Am. Chem. Soc.  1976,  98:  2227 

<A NAME="RT21711SS-17D">17d</A> Khanna RN. Singh KP. Sharma J. Org. Prep. Proced. Int.  1992,  6:  687 

<A NAME="RT21711SS-18">18</A> Perrin DD. Armarego WLF. In Purification of Laboratory Chemicals   3rd ed.:  Butterworth-Heinemann Ltd; Oxford: 1988. 

<A NAME="RT21711SS-19">19</A>

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