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For type II intramolecular Diels-Alder reactions, see B. R. Bear, S. M. Sparks, K. J. Shea, Angew. Chem. 2001, 113, 864-894;
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6
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84987344264
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Examples for the bridged-type intramolecular Diels-Alder reaction were reported using cyclohexadienone as a dienophile unit. The Z-configuration of the diene part facilitates a suitable transition state for the bridged-type reaction, a) H. Greuter, G. Fráter, H. Schmid, Helv. Chim. Acta 1972, 55, 526-531;
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Greuter, H.1
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d) H. Greuter, H. Schmid, G. Fráter, Helv. Chim. Acta 1977, 60, 1701-1729;
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Greuter, H.1
Schmid, H.2
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11
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0001819645
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For the formation of the bridged-type Diels-Alder product as a minor product, see a) E. J. Corey, M. Petrzilka, Tetrahedron Lett. 1975, 2537-2540;
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e) D. Craig, M. J. Ford, R. S. Gordon, J. A. Stones, A. J. P. White, D. J. Williams, Tetrahedron 1999, 55, 15045-15066.
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Craig, D.1
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N. Iwasawa, F. Sakurada, M. Iwamoto, Org. Lett. 2000, 2, 871-873.
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b) K. Tanino, F. Kondo, T. Shimizu, M. Miyashita, Org. Lett. 2002, 4, 2217-2219;
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c) D. G. J. Young, J. A. Burlison, U. Peters, J. Org. Chem. 2003, 68, 3494-3497;
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1642293104
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d) T. Baba, S. Takai, N. Sawada, M. Isobe, Synlett 2004, 603-608.
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22
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0037012896
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A related intramolecular Diels-Alder reaction of a siloxydiene derivative, which gave a fused-type product selectively in spite of its electronic bias, was reported: K. Takasu, S. Mizutani, M. Ihara, J. Org. Chem. 2002, 67, 2881-2884.
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Takasu, K.1
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24
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28044470027
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CCDC-276360 (for adduct 2) and CCDC-276361 (for adduct 11) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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-
-
-
25
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0033582585
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[8] For examples of fused-type cycloadditions, see a) M. Ihara, K. Makita, K. Takasu, J. Org. Chem. 1999, 64, 1259-1264;
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Ihara, M.1
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27
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33748234272
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and references therein
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Angew. Chem. Int. Ed. Engl. 1993, 32, 1010-1022, and references therein.
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28
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33845184602
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P. V. Bonnesen, C. L. Puckett, R. V. Honeychuck, W. H. Hersh, J. Am. Chem. Soc. 1989, 111, 6070-6081.
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29
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28044437476
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note
-
Product 13 was obtained as a single stereoisomer; the relative configuration has not yet been determined.
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32
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0036214835
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S. Takai, P. Ploypradith, A. Hamajima, K. Kira, M. Isobe, Synlett 2002, 588-592.
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Takai, S.1
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