{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T01:12:35Z","timestamp":1760404355021},"reference-count":23,"publisher":"CLOCKSS Archive","issue":"12","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["HETEROCYCLES"],"published-print":{"date-parts":[[2002]]},"DOI":"10.3987\/com-02-9594","type":"journal-article","created":{"date-parts":[[2009,3,9]],"date-time":"2009-03-09T04:01:45Z","timestamp":1236571305000},"page":"2261","source":"Crossref","is-referenced-by-count":13,"title":["Palladium-catalyzed Synthesis of 2,2-Dimethyl-3-pyrrolines from a-Aminoallene and Aryl Iodides"],"prefix":"10.13030","volume":"57","author":[{"given":"Takanori","family":"Shibata","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Takanori","family":"Shibata","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sho","family":"Kadowaki","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kentaro","family":"Takagi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"5187","reference":[{"key":"#cr-split#-10.3987\/COM-02-9594-1.1","doi-asserted-by":"crossref","unstructured":"Recent reviews, see: (a) Y. Yamamoto and U. Radhakrishnan, Chem. Soc. Rev., 1999, 28, 199.","DOI":"10.1039\/a806581k"},{"key":"#cr-split#-10.3987\/COM-02-9594-1.2","doi-asserted-by":"crossref","unstructured":"(b) A. S. K. Hashmi, Angew. Chem., Int. Ed., 2000, 39, 3590.","DOI":"10.1002\/1521-3773(20001016)39:20<3590::AID-ANIE3590>3.0.CO;2-L"},{"key":"#cr-split#-10.3987\/COM-02-9594-2.1","doi-asserted-by":"crossref","unstructured":"Reviews, see: (a) Y. Tamaru and M. Kimura, Synlett, 1997, 749.","DOI":"10.1055\/s-1997-5744"},{"key":"#cr-split#-10.3987\/COM-02-9594-2.2","doi-asserted-by":"crossref","unstructured":"(b) M. Frederickson and R. Grigg, Org. Prep. Proced. Int., 1997, 29, 63.","DOI":"10.1080\/00304949709355173"},{"key":"#cr-split#-10.3987\/COM-02-9594-2.3","doi-asserted-by":"crossref","unstructured":"(c) R. Zimmer, C. U. Dinesh, E. Nadanan, and F. A. Hhan, Chem. Rev., 2000, 100, 3067.","DOI":"10.1021\/cr9902796"},{"key":"10.3987\/COM-02-9594-3","doi-asserted-by":"crossref","unstructured":"3. A pioneering work of palladium-catalyzed intermolecular amination of allenes, see: I. Shimizu and J. Tsuji, Chem. Lett., 1984, 233.","DOI":"10.1246\/cl.1984.233"},{"key":"#cr-split#-10.3987\/COM-02-9594-4.1","doi-asserted-by":"crossref","unstructured":"Recent examples, see: (a) M. Meguro, Y. Yamamoto, and H. Ohno, Tetrahedron Lett., 1998, 39, 5421.","DOI":"10.1016\/S0040-4039(98)01044-2"},{"key":"#cr-split#-10.3987\/COM-02-9594-4.2","doi-asserted-by":"crossref","unstructured":"(b) A. Toda, Y. Miwa, T. Taga, E. Osawa, Y. Yamaoka, N. Fujii, and T. Ibuka, J. Org. Chem., 1999, 64, 2992.","DOI":"10.1021\/jo9901687"},{"key":"#cr-split#-10.3987\/COM-02-9594-4.3","doi-asserted-by":"crossref","unstructured":"(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.","DOI":"10.1021\/ol990700c"},{"key":"#cr-split#-10.3987\/COM-02-9594-4.4","doi-asserted-by":"crossref","unstructured":"(d) M. Anzai, A. Toda, H. Ohno, Y. Takemoto, N. Fujii, and T. Ibuka, Tetrahedron Lett., 1999, 40, 7393.","DOI":"10.1016\/S0040-4039(99)01517-8"},{"key":"#cr-split#-10.3987\/COM-02-9594-4.5","doi-asserted-by":"crossref","unstructured":"(e) R. Grigg, A. Liu, D. Shaw, S. Suganthan, D. E. Woodall, and G. Yoganathan, Tetrahedron Lett., 2000, 41, 7125.","DOI":"10.1016\/S0040-4039(00)01176-X"},{"key":"#cr-split#-10.3987\/COM-02-9594-4.6","doi-asserted-by":"crossref","unstructured":"(f) R. K. Dieter and H. Yu, Org. Lett., 2001, 3, 3855.","DOI":"10.1021\/ol016654+"},{"key":"#cr-split#-10.3987\/COM-02-9594-4.7","doi-asserted-by":"crossref","unstructured":"(g) S.-K. Kang and K.-J. Kim, Org. Lett., 2001, 3, 511.","DOI":"10.1021\/ol006796o"},{"key":"#cr-split#-10.3987\/COM-02-9594-4.8","doi-asserted-by":"crossref","unstructured":"(h) H. Ohno, M. Anzai, A. Toda, S. Ohishi, N. Fujii, T. Tanaka, Y. Takemoto, and T. Ibuka, J. Org. Chem., 2001, 66, 4904.","DOI":"10.1021\/jo015683v"},{"key":"10.3987\/COM-02-9594-5","doi-asserted-by":"crossref","unstructured":"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.","DOI":"10.1021\/ja002225f"},{"key":"#cr-split#-10.3987\/COM-02-9594-6.1","doi-asserted-by":"crossref","unstructured":"A rare example of synthesis of 2,2-dimethyl-3-pyrrolines, see: (a) H.-J. Weintz and P. Binger, Tetrahedron Lett., 1985, 26, 4075.","DOI":"10.1016\/S0040-4039(00)89296-5"},{"key":"#cr-split#-10.3987\/COM-02-9594-6.2","doi-asserted-by":"crossref","unstructured":"(b) M. Kimura, H. Harayama, S. Tanaka, and Y. Tamaru, J. Chem. Soc., Chem. Commun., 1994, 2531.","DOI":"10.1039\/c39940002531"},{"key":"10.3987\/COM-02-9594-7","unstructured":"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 \u03b1-aminoallene."},{"key":"#cr-split#-10.3987\/COM-02-9594-8.1","doi-asserted-by":"crossref","unstructured":"(a) S. Murahashi, Y. Imada, Y. Taniguchi, and S. Higashiura, J. Org. Chem., 1993, 58, 1538.","DOI":"10.1021\/jo00058a040"},{"key":"#cr-split#-10.3987\/COM-02-9594-8.2","doi-asserted-by":"crossref","unstructured":"(b) Y. Hashimoto, Y. Horie, M. Hayashi, and K. Saigo, Tetrahedron: Asymmetry, 2000, 11, 2205.","DOI":"10.1016\/S0957-4166(00)00157-9"},{"key":"#cr-split#-10.3987\/COM-02-9594-9.1","doi-asserted-by":"crossref","unstructured":"(a) R. Grigg, W. S. MacLachlan, D. T. MacPherson, V. Sridharan, S. 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