Palladium-catalyzed synthesis of 2,2-dimethyl-3-pyrrolines from α-aminoallene and aryl iodides

Heterocycles

Volumn 57, Issue 12, 2002, Pages 2261-2266

  Shibata, Takanori ^a   Kadowaki, Sho ^a   Takagi, Kentaro ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CARBON MONOXIDE; IODINE DERIVATIVE; PALLADIUM; PYRROLINE DERIVATIVE;

ARTICLE; ATMOSPHERIC PRESSURE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0036901055     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-02-9594     Document Type: Article

References (25)

1. (a) Y. Yamamoto and U. Radhakrishnan, Chem. Soc. Rev., 1999, 28, 199.
2. (b) A. S. K. Hashmi, Angew. Chem., Int. Ed., 2000, 39, 3590.
3. (a) Y. Tamaru and M. Kimura, Synlett, 1997, 749.
4. (b) M. Frederickson and R. Grigg, Org. Prep. Proced. Int., 1997, 29, 63.
5. (c) R. Zimmer, C. U. Dinesh, E. Nadanan, and F. A. Hhan, Chem. Rev., 2000, 100, 3067.
6. A pioneering work of palladium-catalyzed intermolecular amination of allenes, see: I. Shimizu and J. Tsuji, Chem. Lett., 1984, 233.
7. (a) M. Meguro, Y. Yamamoto, and H. Ohno, Tetrahedron Lett., 1998, 39, 5421.
8. (b) A. Toda, Y. Miwa, T. Taga, E. Osawa, Y. Yamaoka, N. Fujii, and T. Ibuka, J. Org. Chem., 1999, 64, 2992.
9. (c) F. P. J. T. Rutjes, K. C. M. F. Tjen, L. B. Wolf, W. F. J. Karstens, H. E. Schoemaker, and H, Hiemstra, Org. Lett., 1999, 1, 717.
10. (d) M. Anzai, A. Toda, H. Ohno, Y. Takemoto, N. Fujii, and T. Ibuka, Tetrahedron Lett., 1999, 40, 7393.
11. (e) R. Grigg, A. Liu, D. Shaw, S. Suganthan, D. E. Woodall, and G. Yoganathan, Tetrahedron Lett., 2000, 41, 7125.
12. (f) R. K. Dieter and H. Yu, Org. Lett., 2001, 3, 3855.
13. (g) S.-K. Kang and K.-J. Kim, Org. Lett., 2001, 3, 511.
14. (h) H. Ohno, M. Anzai, A. Toda, S. Ohishi, N. Fujii, T. Tanaka, Y. Takemoto, and T. Ibuka, J. Org. Chem., 2001, 66, 4904.
15. Other transition metal complex-mediated syntheses of 3-pyrrolines, see: G. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1992, 114, 7324. (b) H. Kagoshima and T. Akiyama, J. Am. Chem. Soc., 2000, 122, 11741. (c) M. P. Green, J. C. Prodger, A. E. Sherlock, and C. J. Hayes, Org. Lett., 3, 3377.
16. Other transition metal complex-mediated syntheses of 3-pyrrolines, see: G. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1992, 114, 7324. (b) H. Kagoshima and T. Akiyama, J. Am. Chem. Soc., 2000, 122, 11741. (c) M. P. Green, J. C. Prodger, A. E. Sherlock, and C. J. Hayes, Org. Lett., 3, 3377.
17. Other transition metal complex-mediated syntheses of 3-pyrrolines, see: G. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1992, 114, 7324. (b) H. Kagoshima and T. Akiyama, J. Am. Chem. Soc., 2000, 122, 11741. (c) M. P. Green, J. C. Prodger, A. E. Sherlock, and C. J. Hayes, Org. Lett., 3, 3377.
18. A rare example of synthesis of 2,2-dimethyl-3-pyrrolines, see: (a) H.-J. Weintz and P. Binger, Tetrahedron Lett., 1985, 26, 4075. (b) M. Kimura, H. Harayama, S. Tanaka, and Y. Tamaru, J. Chem. Soc., Chem. Commun., 1994, 2531.
19. A rare example of synthesis of 2,2-dimethyl-3-pyrrolines, see: (a) H.-J. Weintz and P. Binger, Tetrahedron Lett., 1985, 26, 4075. (b) M. Kimura, H. Harayama, S. Tanaka, and Y. Tamaru, J. Chem. Soc., Chem. Commun., 1994, 2531.
20. As a preliminary experiment, we investigated the effect of substituents on nitrogen using buta-2,3-dienylamine. By the palladium catalyzed reaction with iodobenzene, 2,2-unsubstituted pyrroline derivative was obtained (ca. 20%) from N-benzylbuta-2,3-dienylamine but not from N-tosyl or N-(4- methoxyphenyl)buta-2,3-dienylamine. We decided benzyl as a protecting group for nitrogen of α aminoallene.
21. (a) S. Murahashi, Y. Imada, Y. Taniguchi, and S. Higashiura, J. Org. Chem., 1993, 58, 1538.
22. (b) Y. Hashimoto, Y. Horie, M. Hayashi, and K. Saigo, Tetrahedron: Asymmetry, 2000, 11, 2205.
23. (a) R. Grigg, W. S. MacLachlan, D. T. MacPherson, V. Sridharan, S. Suganthan, M. Thornton-Pett, and J. Zhang, Tetrahedron, 2000, 56, 6585.
24. (b) R. Grigg, A. Liu, D. Shaw, S. Suganthan, D. E. Woodall, and G. Yoganathan, Tetrahedron Lett., 2000, 41, 7125.
25. G. J. Gordon, T. Luker, M. W. Tuckett, R. J. Whitby, and J. Richard, Tetrahedron, 2000, 56, 2113.