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Synthesis 2006(21): 3605-3610
DOI: 10.1055/s-2006-950215
DOI: 10.1055/s-2006-950215
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Multifunctionalized Furans from Diazoallenes: Rearrangement of 6-Methylenebicyclo[3.1.0]hexanes
Further Information
Received
30 May 2006
Publication Date:
21 August 2006 (online)
Publication History
Publication Date:
21 August 2006 (online)
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.
Key words
diazoallene - [3+2] cycloaddition - multifunctionalized furans
- 1
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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
References
The diazoallene compounds were found to be unstable using EI techniques for mass spectrometry measurements.