Stereocontrolled syntheses of cis-decalin and bicyclo[4.2.2]dec-7-en-4-one derivatives from 2-methoxyphenols. First examples of two-carbon ring expansion of 2-vinylbicyclo[2.2.2]octenols

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5897-5900

  Lee, Tsung Ho ^a   Liao, Chun Chen ^a   Liu, Wen Cheng ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

anionic oxy Cope rearrangement; anionic 1,3 rearrangement; bicyclo 4.2.2 decenone; cis decalin; ring expansion

Indexed keywords

BICYCLO COMPOUND; BICYCLO[2.2.2]OCTANE DERIVATIVE; DECALIN; DECALIN DERIVATIVE; GUAIACOL; VINYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0030581359     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01271-3     Document Type: Article

References (12)

1. 1. (a) Paquette, L. A.; Elmore, S. W. J. Org. Chem. 1995, 60, 889-896.
2. (b) Paquette, L. A.; Su, Z.; Bailey, S.; Montgomery, F. J. J. Org. Chem. 1995, 60, 897-902.
3. 2. (a) Paqutte, L. A. Angew. Chem. Int. Ed. Engl. 1990, 29, 609-626.
4. (b) Richard, K. H. in Comprehensive Organic Synthesis; Paqutte, L. A., Ed.; Pergamon Press : Oxford, 1991; Vol. 5 Chap. 7.
5. 3. Berson, J. A.; Jones, M. Jr. J. Am. Chem. Soc. 1964, 86, 5017-5018 and 5019-5020.
6. 4. Evans, D. A.; Golob, A. M. J. Am. Chem. Soc. 1975, 97, 4765-4766.
7. 5. Chu, C. S.; Lee, T. H.; Liao, C. C. Synlett 1994, 635-636.
8. 6. The reaction conditions have not yet been optimized to increase stereoselectivities.
9. 7. Both the syn isomers of 11 and 13 underwent [3,3] anionic oxy-Cope rearrangement.
10. 8. The result will be published in a full paper in the future. We thank professor Shie-Ming Peng and Mr. Gene-Hsiang Lee for the X-ray diffraction study.
11. 9. Ley, S. V.; Merritt, A. T. Natural Product Reports 1992, 9, 243-287.
12. 10. Cimino, G.; De Stefano, S.; Guerriero, A.; Minale, L. Tetrahedron Lett. 1975, 17, 1425-1428.