Synthesis of Multifunctionalized Furans from Diazoallenes: Rearrangement of 6-Methylenebicyclo[3.1.0]hexanes

Abstract

The synthesis of annulated tetrasubstituted furans using diazoallene precursors is described. This reaction provides efficient access to synthetically useful furan intermediates, which are otherwise difficult to obtain.

diazoallene - [3+2] cycloaddition - multifunctionalized furans

References

<A NAME="RZ10506SS-1">1</A> Joule JA. Mills K. Heterocyclic Chemistry   4th ed., Blackwell; Oxford: 2000.  p.296 

<A NAME="RZ10506SS-2">2</A> For an application to annulated furan synthesis, see: Zambias R. Caldwell C. Kopka I. Hammond M. J. Org. Chem.  1988,  53:  4135 

<A NAME="RZ10506SS-3">3</A> Koenig B. In Science of Synthesis   Vol. 9:  Maas G. Thieme; Stuttgart: 2002.  p.183 

For recent reports from our group in this regard, see:

<A NAME="RZ10506SS-4A">4a</A> Bhanu Prasad BA. Yoshimoto FK. Sarpong R. J. Am. Chem. Soc.  2005,  127:  12468 

<A NAME="RZ10506SS-4B">4b</A> Pujanauski B. G., Bhanu Prasad B. A., Sarpong R.; J. Am. Chem. Soc.; 2006, 128: 6786

<A NAME="RZ10506SS-5">5</A> For a pertinent, recent review on the trimethylmethylene-methane diyl, see: Allan AK. Carroll GL. Little RD. Eur. J. Org. Chem.  1998,  1 

<A NAME="RZ10506SS-6">6</A> Myers AG. Zheng B. J. Am. Chem. Soc.  1996,  118:  4492 

<A NAME="RZ10506SS-7">7</A> See, for example: Hughes CC. Kennedy-Smith JJ. Trauner D. Org. Lett.  2003,  5:  4113 

<A NAME="RZ10506SS-8">8</A>

The diazoallene compounds were found to be unstable using EI techniques for mass spectrometry measurements.