Study of cis/trans and endo/exo diastereoselectivity in the [4+3]-cycloaddition reaction of 2-functionalized furans and dimethyloxyallyl cation: Preparation of versatile cycloheptane synthons

Chemistry Letters

Volumn , Issue 9, 1997, Pages 847-848

  Montaña, Angel M ^a   Ribes, Sandra ^a   Grima, Pedro M ^a   Garcia, Francisca ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031317077     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.847     Document Type: Article

References (19)

1. a) R. Noyori and Y. Hayakawa: Reductive Dehalogenation of Polyhaloketones. In Organic Reactions, W.G. Dauben editor; John Wiley and Sons, Ltd., New York (1983), Vol. 29, pp. 163-343.
2. b) J. Mann, Tetrahedron, 42, 4611, (1986).
3. c) L.C. Almeida Barbosa and J. Mann, Synthesis, 1996, 31.
4. a) M.R. Ashcroft and H.M.R. Hoffmann, Organic Syntheses, 58, 17, (1978).
5. b) H.M.R. Hoffmann, Angew., 20, 877, (1973).
6. c) H.M.R. Hoffmann, Angew. Int. Ed. Eng., 23, 1, (1984).
7. R. Noyori and Y. Hayakawa, Tetrahedron, 41, 5879, (1985).
8. a) A.Hosomi and Y. Tominaga: [4+3] Cycloadditions. In Comprehensive Organic Chemistry, Edited by B. Trost and I. Fleming, Pergamon Press, Oxford (1995), Vol 5, pp. 593-615.
9. b) S.J. Jin, JR Choi, J. Oh, D. Lee and J.K. Cha, J. Am. Chem. Soc., 117, 10914, (1995); and references therein cited.
10. P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon Press, New York (1983), pp.2-53.
11. Commercially available furans.
12. J. E. Fitzpatrick, D.J. Milner and P. White, Synth. Commun., 2, 489 (1982).
13. S. Pelter, M. Rowlands and G. Clements, Synthesis, 1897, 51.
14. Prepared from furoyl chloride and cyclohexanol
15. L.F. Fieser and R. Stevenson, J. Am. Chem. Soc. 76, 1731, (1954).
16. M. Bednaiski and S. Danishefsky, J Am. Chem. Soc., 105, 3716(1986).
17. O.E.O. Hormi and J.H. Näsman, Synth. Commun., 16, 69, (1986).
18. J. H. Näsman, Synthesis, 1985, 788.
19. Conversions of furan substrates and yields of cycloadducts are not optimized. All reactions were carried out under the same standard conditions for comparative purposes. Conversion was evaluated by GC in front of a standard along 20 h of reaction time, unless the reaction was complete before.