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

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2 For an application to annulated furan synthesis, see: Zambias R. Caldwell C. Kopka I. Hammond M. J. Org. Chem.  1988,  53:  4135 

3 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:

4a Bhanu Prasad BA. Yoshimoto FK. Sarpong R. J. Am. Chem. Soc.  2005,  127:  12468 

4b Pujanauski B. G., Bhanu Prasad B. A., Sarpong R.; J. Am. Chem. Soc.; 2006, 128: 6786

5 For a pertinent, recent review on the trimethylmethylene-methane diyl, see: Allan AK. Carroll GL. Little RD. Eur. J. Org. Chem.  1998,  1 

6 Myers AG. Zheng B. J. Am. Chem. Soc.  1996,  118:  4492 

7 See, for example: Hughes CC. Kennedy-Smith JJ. Trauner D. Org. Lett.  2003,  5:  4113 

8

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