none 10.3987/COM-02-9594 CLOCKSS Archive CLOCKSS Archive 5187 36504514 73640 20090309112757 10.13030 2024-06-24T20:34:40Z 2009-03-09T04:01:45Z 13 HETEROCYCLES HETEROCYCLES 0385-5414 HTCYAM 2002 57 12 Takanori Shibata Takanori Shibata Sho Kadowaki Kentaro Takagi 2002 2261 COM-02-9594 10.3987/COM-02-9594 20090309112757 https://triggered.stanford.clockss.org/ServeContent?doi=10.3987%2Fcom-02-9594 https://triggered.edinburgh.clockss.org/ServeContent?doi=10.3987%2Fcom-02-9594 10.1039/a806581k Recent reviews, see: (a) Y. Yamamoto and U. Radhakrishnan, Chem. Soc. Rev., 1999, 28, 199. 10.1002/1521-3773(20001016)39:20<3590::AID-ANIE3590>3.0.CO;2-L (b) A. S. K. Hashmi, Angew. Chem., Int. Ed., 2000, 39, 3590. 10.1055/s-1997-5744 Reviews, see: (a) Y. Tamaru and M. Kimura, Synlett, 1997, 749. 10.1080/00304949709355173 (b) M. Frederickson and R. Grigg, Org. Prep. Proced. Int., 1997, 29, 63. 10.1021/cr9902796 (c) R. Zimmer, C. U. Dinesh, E. Nadanan, and F. A. Hhan, Chem. Rev., 2000, 100, 3067. 10.1246/cl.1984.233 3. A pioneering work of palladium-catalyzed intermolecular amination of allenes, see: I. Shimizu and J. Tsuji, Chem. Lett., 1984, 233. 10.1016/S0040-4039(98)01044-2 Recent examples, see: (a) M. Meguro, Y. Yamamoto, and H. Ohno, Tetrahedron Lett., 1998, 39, 5421. 10.1021/jo9901687 (b) A. Toda, Y. Miwa, T. Taga, E. Osawa, Y. Yamaoka, N. Fujii, and T. Ibuka, J. Org. Chem., 1999, 64, 2992. 10.1021/ol990700c (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. 10.1016/S0040-4039(99)01517-8 (d) M. Anzai, A. Toda, H. Ohno, Y. Takemoto, N. Fujii, and T. Ibuka, Tetrahedron Lett., 1999, 40, 7393. 10.1016/S0040-4039(00)01176-X (e) R. Grigg, A. Liu, D. Shaw, S. Suganthan, D. E. Woodall, and G. Yoganathan, Tetrahedron Lett., 2000, 41, 7125. 10.1021/ol016654+ (f) R. K. Dieter and H. Yu, Org. Lett., 2001, 3, 3855. 10.1021/ol006796o (g) S.-K. Kang and K.-J. Kim, Org. Lett., 2001, 3, 511. 10.1021/jo015683v (h) H. Ohno, M. Anzai, A. Toda, S. Ohishi, N. Fujii, T. Tanaka, Y. Takemoto, and T. Ibuka, J. Org. Chem., 2001, 66, 4904. 10.1021/ja002225f 5. 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. 10.1016/S0040-4039(00)89296-5 A rare example of synthesis of 2,2-dimethyl-3-pyrrolines, see: (a) H.-J. Weintz and P. Binger, Tetrahedron Lett., 1985, 26, 4075. 10.1039/c39940002531 (b) M. Kimura, H. Harayama, S. Tanaka, and Y. Tamaru, J. Chem. Soc., Chem. Commun., 1994, 2531. 7. 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. 10.1021/jo00058a040 (a) S. Murahashi, Y. Imada, Y. Taniguchi, and S. Higashiura, J. Org. Chem., 1993, 58, 1538. 10.1016/S0957-4166(00)00157-9 (b) Y. Hashimoto, Y. Horie, M. Hayashi, and K. Saigo, Tetrahedron: Asymmetry, 2000, 11, 2205. 10.1016/S0040-4020(00)00628-1 (a) R. Grigg, W. S. MacLachlan, D. T. MacPherson, V. Sridharan, S. Suganthan, M. Thornton-Pett, and J. Zhang, Tetrahedron, 2000, 56, 6585. 10.1016/S0040-4039(00)01176-X (b) R. Grigg, A. Liu, D. Shaw, S. Suganthan, D. E. Woodall, and G. Yoganathan, Tetrahedron Lett., 2000, 41, 7125. 10.1016/S0040-4020(99)01094-7 10. G. J. Gordon, T. Luker, M. W. Tuckett, R. J. Whitby, and J. Richard, Tetrahedron, 2000, 56, 2113.