First stereoselective inverse demand [4 + 2] cycloaddition reactions of novel chiral allenamides with heterodienes. Preparation of highly functionalized 2-arylpyranyl heterocycles

Organic Letters

Volumn 1, Issue 13, 1999, Pages 2145-2148

  Wei, Lin Li ^a   Hsung, Richard P ^a   Xiong, Hui ^a   Mulder, Jason A ^a   Nkansah, Nancy T ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001703383     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990345q     Document Type: Article

References (30)

1. For reviews, see: (a) Saalfrank, R. W.; Lurz, C. J. In Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; p 3093.
2. (b) Schuster, H. E.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley and Sons: New York, 1984.
3. (a) Hsung, R. P. J. Org. Chem. 1997, 62, 7904.
4. (b) Hsung, R. P. Heterocycles 1998, 48, 421.
5. (c) Granum, K. G.; Merkel, G.; Mulder, J. A.; Debbins, S. A.; Hsung, R. P. Tetrahedron Lett. 1998, 9597.
6. (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.
7. (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.
8. (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.
9. (g) Douglas C. J.; Sklenicka, H.; 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, 13683.
10. (h) Hsung, R. P.; Zificsak, C.; Wei, L.-L.; Zehnder, L.; Park, F.; Kim, M.; Tran, M. J. Org. Chem. 1999, 64, 8736.
11. (a) Wei, L.-L.; Xiong, H.; Douglas, C. J.; Hsung, R. P. Tetrahedron Lett. 1999, 6903.
12. (b) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Douglas, C. J.; Xiong, H.; Mulder, J. A. Org. Lett. 1999, 1, 1237.
13. Dickinson, W. B.; Lang, P. C. Tetrahedron Lett. 1967, 3035.
14. Overman, L. E.; Marlowe, C. K.; Clizbe, L. A. Tetrahedron Lett. 1979, 599.
15. (a) Rádl, S.; Kovárová, L. Collect. Czech. Chern. Commun. 1991, 56, 2413.
16. (b) Reisch, J.; Salehi-Artimani, R. A. J. Heterocycl. Chem. 1989, 26, 1803.
17. Jones, B. C. N. M.; Silverton, J. V.; Simons, C.; Megati, S.; Nishimura, H.; Maeda, Y.; Mitsuya, H.; Zemlicka, J. J. Med. Chem. 1995, 38, 1397.
18. Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 435, and references cited therein.
19. (a) Noguchi, M.; Okada, H.; Wantanabe, M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6851.
20. (b) Farina, V.; Kant, J. Tetrahedron Lett. 1992, 3559 and 3563.
21. Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 9, 10869 and references therein.
22. Close, W. J. J. Org. Chem. 1950, 15, 1131.
23. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77.
24. Sibi's dibenzylidene-substituted oxazolidinone can be purchased from Aldrich. For synthesis, see: (a) Sibi, M. P.; Deshpande, P. K.; Ji, J. G. Tetrahedron Lett. 1995, 8965.
25. (b) Sibi, M. P.; Ji, J. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 190.
26. (c) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163.
27. For another example of this isomerization method, see: Pourcelot, G.; Cadiot, P.; Georgoulis, C. Tetrahedron 1982, 38, 2123.
28. 20D, and MS.
29. Klop, W.; Klusener, P. A. A.; Brandsma, L. Recl. J. R. Neth. Chem. Soc. 1984, 103, 85.
30. For all cycloadducts, chemical shifts of the anomeric proton for major isomers are consistently 0.18-0.40 ppm higher than those from minor isomers.