Lewis acid promoted hetero [2 + 2] cycloaddition reactions of aldehydes with 10-propynyl-9(10h)-acridone. A highly stereoselective synthesis of acrylic acid derivatives and 1,3-dienes using an electron deficient variant of ynamine

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1237-1240

  Hsung, Richard P ^a   Zificsak, Craig A ^a   Wei, Lin Li ^a   Douglas, Christopher J ^a   Xiong, Hui ^a   Mulder, Jason A ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001541454     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990211c     Document Type: Article

References (29)

1. UMN Undergraduate Research Participant: 1998-1999. The recipient of 1998 Pharmacia-Upjohn and UMN Department of Chemistry Lando/ NSF Program for Summer Research Fellowship.
2. For reviews on chemistry of ynamines, see: (a) Ficini, J. Tetrahedron 1976, 32, 1448.
3. (b) Himbert, G. Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; pp 3267-3443.
4. For recent examples, see: (a) Imbriglio, J.; Rainier, J. Abstracts of Papers, 217th National Meeting of the American Chemical Society, Anaheim, CA, Spring 1999; American Chemical Society: Washington, DC, 1999; ORGN-502.
5. (b) Bernstein, R.; Foote, C. S. Tetrahedron Lett. 1998, 7051.
6. (c) Witulski, B.; Stengel, T. Angew. Chem. Int. Ed. Engl. 1998, 37, 489.
7. (d) Bloxham, J.; Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1993, 3055.
8. (e) Padwa, A.; Gareau, Y.; Harrison, B.; Rodriguez, A. J. Org. Chem. 1992, 57, 3540.
9. Wei, L.-L.; Xiong, H.; Douglas, C. J.; Hsung, R. P. Tetrahedron Lett. 1999, 6903.
10. (a) Hsung, R. P. J. Org. Chem. 1997, 62, 7904.
11. (b) Hsung, R. P. Heterocycles 1998, 48, 421.
12. (c) Granum, K. G.; Merkel, G.; Mulder, J. A.; Debbins, S. A.; Hsung, R. P. Tetrahedron Lett. 1998, 9597.
13. (d) Hsung, R. P.; Shen, H. C.; Douglas, C. J.; Morgan, C. D.; Degen, S. J.; Yao, L. J. J. Org Chem. 1999, 64, 690.
14. (e) Degen, S. J.; Mueller, K. L.; Shen, H. C.; Mulder, J. A.; Golding, G. M.; Wei, L.-L.; Zificsak, C. A.; Hsung, R. P. Bioorg. Med. Chem. Lett. 1999, 973.
15. (f) Hsung, R. P.; Wei, L.-L.; Sklenicka, H. M.; Douglas, C. J.; McLaughlin, M. J.; Mulder, J. A.; Yao, L. J. Org. Lett. 1999, 1, 509.
16. (g) Douglas, C. J.; Sklenicka, H. M.; Shen, H. C.; Golding, G. M.; Mathias, D. S.; Degen, S. J.; Morgan, C. D.; Shih, R. A.; Mueller, K. L.; Seurer, L. M.; Johnson, E. W.; Hsung, R. P. Tetrahedron 1999, 55, in press.
17. (a) Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. J. Org. Chem. USSR 1991, 27, 1576.
18. (b) Tikhomirov, D. A.; Eremeev, A. V. Chem. Heterocycl. Compd. 1987, 23, 1141.
19. (c) Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A. Tetrahedron Lett. 1985, 4141.
20. (d) Janousek, Z.; Collard, J.; Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1972, 11, 917.
21. Joshi, R V.; Xu, Z.-Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089.
22. For a related account using ynamines, see: Fuks, R.; Viehe, H. G. Chem. Ber. 1970, 103, 564.
23. (a) Katritzky, A. R.; Ramer, W. H. J. Org. Chem. 1985, 50, 852.
24. (b) Rádl, S.; Kovárová, L. Collect. Czech. Chem. Commun. 1991, 56, 2413.
25. (c) Reisch, J.; Salehi-Artimani, R. A. J. Heterocycl. Chem. 1989, 26, 1803.
26. (d) Mahamoud, A.; Galy, J. P.; Vincent, E. J. Synthesis 1981, 917.
27. We prepared compound 4 from acridone in two high-yielding steps (89% overall). Deprotonated acridone was propargylated with propargyl bromide in THF, and a subsequent isomerization of the terminal alkyne to the ynamide 4 was carried out by using KOH in DMSO at room temperature. Also see ref 9a.
28. Marshall, J. A.; Shearer, B. G.; Crooks, S. L. J. Org. Chem. 1987, 52, 1236.
29. 13C NMR, FTIR, and LRMS (see Supporting Information).