Synthesis and Chemoselective Reactivity of 3-aminocyclopentadienones

Organic Letters

Volumn 1, Issue 12, 1999, Pages 2037-2039

  Rainier, Jon D ^a   Imbriglio, Jason E ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000467222     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9912128     Document Type: Article

References (25)

1. For a discussion of the properties and reactivity of cyclopentadienones, see: Ogliaruso, M. A.; Romanelli, M. G.; Becker, E. I. Chem. Rev. 1965, 65, 261.
2. For a recent example of the dimerization of a non-aryl-substituted cyclopentadienone, see: West, F. G.; Gunawardena, G. U. J. Org. Chem. 1993, 58, 5043.
3. (a) For oxime-protected cyclopentadienones, see: Mackay, D.; Papadopoulos, D.; Taylor, N. J. J. Chem. Soc., Chem. Commun. 1992, 325.
4. (b) For cyclopentadiene-protected cyclopentadienones, see: Dols, P. P. M. A.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1994, 50, 8515 and references therein
5. (c) For a review discussing cyclopentadienones masked as 4-acetoxycyclopentenones, see: Harre, M. Raddatz, P.; Walenta, R.; Winterfeldt, E. Angew. Chem., Int. Ed. Engl. 1982, 21, 480.
6. See ref 1 and (a) Yamashita, Y.; Miyauchi, Y.; Masumura, M. Chem. Lett. 1983 489.
7. (b) Yamashita, Y.; Masumura, M. Tetrahedron Lett. 1979, 1765.
8. For an example of a tetraamine-substituted cyclopentadienone, see: Lepage, T.; Nakasuji, K.; Breslow, R. Tetrahedron Lett. 1985, 26, 5919.
9. For reviews discussing the chemistry of ynamines, see: (a) Ficini, J. Tetrahedron 1976, 32, 1449.
10. (b) Himbert, G. Methoden der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; p 3267.
11. For recent ynamine cycloaddition reactions, see: (a) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489.
12. (b) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426.
13. (c) Witulski, B.; Stengel, T. J. Chem. Soc., Chem. Commun. 1999, 1879.
14. (d) Hsung, R. P.: Zificsak, C. A.; Wei, L.-L.; Douglas, C. J.; Xiong, H.; Mulder, J. A. Org. Lett. 1999, 1, 1237.
15. Both 2,3,5- and 2.3.4-tris(trimethylsilyl)cyclopentadienones are reasonably stable at room temperature. See: Maier, G.; Lage, H. W., Reisenauer, H. P. Angew. Chem., Int. Ed. Engl. 1981, 20, 976.
16. Vollhardt has synthesized the corresponding all-carbon cyclopentadienone. See: Gesing, E. R. F.; Tane, J. P.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1980, 19, 1023.
17. Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds; VCH: Weinheim, 1995.
18. The position of the remaining trimethylsilyl group in 5 was initially determined spectroscopically (NOE experiments) on indolene 7. A subsequent X-ray structure of 8 confirmed this assignment.
19. Cyclopentadienone 5 was stable at 80 °C for up to 24 h in a 1:1 acetonitrile-benzene solution but decomposed to unrecognizable products upon concentration.
20. For the use of cyclopentadienones as dienes in Diels-Alder cycloadditions, see ref 1 and Baraldi, P. G.; Barco, A, Benetti S.; Pollini, G. P.; Polo, E.; Simoni, D. J. Chem. Soc., Chem. Commun. 1984, 1049.
21. A similar vinylogous ester was unreactive in analogous cycloaddition reactions. See: Herndon, J. W.; Patel, P. P. Tetrahedron Lett. 1997, 38, 59.
22. For an example of the use of an enamine in a hetero-Diels-Alder cycloaddition reaction, see: Stork, G.; Landesman, H. K. J. Am. Chem. Soc. 1956, 78, 5129.
23. For the use of cyclopentadienones as 2π components in cycloaddition chemistry, see ref 1 and (a) Gavina, F.; Costero, A. M.; Gil, P., Palazon, B.; Luis, S. V. J. Am. Chem. Soc. 1981, 103, 1797.
24. (b) Depuy C. H.; Isaks, M.; Eilers, K. L.; Morris, G. F. J. Org. Chem. 1964, 29, 3503.
25. Herndon has been able to carry out the in situ protonation of the corresponding reduced vinylogous esters, see: Herndon, J. W.; Zhu, J. Org. Lett. 1999, 1, 15 and references contained therein.