Synthesis of multifunctionalized furans from diazoallenes: Rearrangement of 6-methylenebicyclo[3.1.0] hexanes

Synthesis

Volumn , Issue 21, 2006, Pages 3605-3610

  Yao, Tuanli ^a   Hong, Allen ^a   Sarpong, Richmond ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

3+2 cycloaddition; Diazoallene; Multifunctionalized furans

Indexed keywords

ADDITION REACTIONS; PARAFFINS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLOADDITION; DIAZOALLENE; MULTIFUNCTIONALIZED FURANS;

AROMATIC COMPOUNDS;

6 METHYLENEBICYCLO[3.1.0]HEXANE DERIVATIVE; ALLENE DERIVATIVE; DIAZOLLENE DERIVATIVE; FURAN DERIVATIVE; HEXANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33751321644     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950215     Document Type: Article

References (9)

1. Joule, J. A.; Mills, K. Heterocyclic Chemistry; 4th ed., Blackwell: Oxford, 2000, 296.
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., Ed.; Thieme: Stuttgart, 2002, 183.
4. For recent reports from our group in this regard, see: (a) Bhanu Prasad, B. A.; Yoshimoto, F. K.; Sarpong, R. J. Am. Chem. Soc. 2005, 127, 12468.
5. (b) Pujanauski B. G., Bhanu Prasad B. A., Sarpong R.; J. Am. Chem. Soc.; 2006, 128: 6786.
6. For a pertinent, recent review on the trimethylmethylene-methane diyl, see: Allan, A. K.; Carroll, G. L.; Little, R. D. Eur. J. Org. Chem. 1998, 1.
7. Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492.
8. See, for example: Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113.
9. The diazoallene compounds were found to be unstable using EI techniques for mass spectrometry measurements.