Complexation-initiated intramolecular diels-alder reaction

Organic Letters

Volumn 2, Issue 6, 2000, Pages 871-873

  Iwasawa, Nobuharu ^a   Sakurada, Fumiko ^a,b   Iwamoto, Mari ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000728738     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005650m     Document Type: Article

References (23)

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3. (c) Kemmitt, R. D. W.; Russell, D. R. In Comprehensive Organometallic Chemistry; Wilkinson G., Ed.; Pergamon Press: Oxford, 1982; Vol. 5, p 1.
4. Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179.
5. Seyferth, D.; Williams, G. H.; Traficante, D. D. J. Am. Chem. Soc. 1974, 96, 604.
6. It is necessary to carry out the elution rapidly because rapid equilibration occurs on silica gel. To achieve clean separation, it is better to cool the column to 0°C.
7. The stereochemistry of the adducts 3a and 3b was determined to be as shown in 3 on the basis of proton coupling constants.
8. Acceleration of the intramolecular Diels-Alder reaction of furan derivatives by absorbing the substrate on silica gel or Florisil has several precedents. See the following examples: (a) Clercq, P. J. D.; Royen, L. A. V. Synth. Commun. 1979, 9, 771.
9. (b) Wang, W. B.; Roskamp, E. J. Tetrahedron Lett. 1992, 33, 7631.
10. (c) Rogers, C.; Keay, B. A. Can. J. Chem. 1993, 71, 611.
11. 1H NMR spectra. 6b was obtained as a mixture of diastereomers in about a 3:1 ratio. The major isomer has the same stereochemistry as that of 3.
12. Seven-membered ring formation by the intramolecular Diels-Alder reaction of furan derivatives is difficult, and only a few examples are known. See for examples: (a) Parker, K. A.; Adamchuk, M. R. Tetrahedron Lett. 1978, 1689.
13. (b) Harwood, L. M.; Jackson, B.; Jones, G.; Prout, G.; Thomas, R. M.; Witt, F. J. J. Chem. Soc., Chem. Commun. 1990, 608.
14. 6 complexes has several precedents, where in almost all cases a Nicholas-type reaction was employed for the cyclization. See for example: (a) Nakamura, T.; Matsui, T.; Tanino, K.; Kuwajima, I. J. Org. Chem. 1997, 62, 3032.
15. (b) Isobe, M.; Hosokawa, S.; Kira, K. Chem. Lett. 1996, 473.
16. (c) Tanaka, S.; Isobe, M. Synthesis 1995, 859.
17. (d) Caddick, S.; Delisser, V. M. Tetrahedron Lett. 1997, 38, 2355.
18. (e) Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 4353.
19. (f) Magnus, P.; Miknis, G. F.; Press: N. J.; Grandjean, D.; Taylor G. M.; Harling, J. J. Am. Chem. Soc. 1997, 119, 6739.
20. (g) Green, J. R. Chem. Commun. 1998, 1751.
21. (h) Iwasawa, N.; Satoh, H. J. Am. Chem. Soc. 1999, 121, 7951.
22. (a) Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II, Vol 12: Transition Metal Alkyne Complexes: Transition Metal-stabilized Propargyl System; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; p 685.
23. (b) Schore, N. E. In Comprehensive Organometallic Chemistry II, Vol 12: Transition Metal Alkyne Complexes: Pauson-Khand Reaction: Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; p 703.