A facile approach to 2-CF3-substituted seven-membered oxacycles via stereoselective preparation and cope rearrangement of 2-CF 3-cis-2,3-bis(alkenyl)oxiranes

Chemistry Letters

Volumn 33, Issue 4, 2004, Pages 438-439

  Shimizu, Masaki ^a   Fujimoto, Takuya ^a   Liu, Xinyu ^a   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; ETHYLENE OXIDE DERIVATIVE; OXEPANE DERIVATIVE; OXEPINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COPE REARRANGEMENT; OXIDATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 3142740405     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.438     Document Type: Article

References (15)

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9. Treatment of 4 with LiTMP followed by the addition of vinyllithium resulted in the production of complex mixture.
10. Cis/trans isomers of 5e, 5i, and 5q were not separable by column chromatography on silica gel or gel permeation chromatography.
11. Review on Cope rearrangement of bis(alkenyl)oxiranes: a) T. Hudlicky, R. Fan, J. W. Reed, and K. G. Gadamasetti, in "Org. React.," John Wiley & Sons, Inc., New York (1992), Vol. 41, p 1.
12. Examples: b) P. v. Zezschwitz, K. Voigt, A. Lansky, M. Noltemeyer, and A. d. Meijere, J. Org. Chem., 64, 3806 (1999).
13. c) W.-N. Chou, J. B. White, and W. B. Smith, J. Am. Chem. Soc., 114, 4658 (1992).
14. Stereochemistry of 6p was not determined at present.
15. cis-Stereochemistry was assigned by NOE experiment.