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For leading references for reaction of vinylic sulfoxides, see: Mase, N.; Watanabe, Y.; Toru, T.; Kakumoto, T.; Hagiwara, T. J. Org. Chem. 2000, 65, 7083-7090. Maezaki, N.; Izumi, M.; Yuyama, S.; Sawamoto, H.; Iwata, C.; Tanaka, T. Tetrahedron 2000, 56, 7927-7945. Abe, H.; Tsuchida, D.; Kashino, S.; Takeuchi, Y.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 833-837. Midura, W. H.; Krysiak, J. A.; Mikolajczyk, M. Tetrahedron 1999, 55, 14791-14802. Priego, J.; Carretero, J. C. Synlett 1999, 1603-1605. Buezo, N. D.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129-7130.
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For leading references for reaction of vinylic sulfoxides, see: Mase, N.; Watanabe, Y.; Toru, T.; Kakumoto, T.; Hagiwara, T. J. Org. Chem. 2000, 65, 7083-7090. Maezaki, N.; Izumi, M.; Yuyama, S.; Sawamoto, H.; Iwata, C.; Tanaka, T. Tetrahedron 2000, 56, 7927-7945. Abe, H.; Tsuchida, D.; Kashino, S.; Takeuchi, Y.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 833-837. Midura, W. H.; Krysiak, J. A.; Mikolajczyk, M. Tetrahedron 1999, 55, 14791-14802. Priego, J.; Carretero, J. C. Synlett 1999, 1603-1605. Buezo, N. D.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129-7130.
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13
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For leading references for reaction of vinylic sulfoxides, see: Mase, N.; Watanabe, Y.; Toru, T.; Kakumoto, T.; Hagiwara, T. J. Org. Chem. 2000, 65, 7083-7090. Maezaki, N.; Izumi, M.; Yuyama, S.; Sawamoto, H.; Iwata, C.; Tanaka, T. Tetrahedron 2000, 56, 7927-7945. Abe, H.; Tsuchida, D.; Kashino, S.; Takeuchi, Y.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 833-837. Midura, W. H.; Krysiak, J. A.; Mikolajczyk, M. Tetrahedron 1999, 55, 14791-14802. Priego, J.; Carretero, J. C. Synlett 1999, 1603-1605. Buezo, N. D.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129-7130.
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14
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For leading references for reaction of vinylic sulfoxides, see: Mase, N.; Watanabe, Y.; Toru, T.; Kakumoto, T.; Hagiwara, T. J. Org. Chem. 2000, 65, 7083-7090. Maezaki, N.; Izumi, M.; Yuyama, S.; Sawamoto, H.; Iwata, C.; Tanaka, T. Tetrahedron 2000, 56, 7927-7945. Abe, H.; Tsuchida, D.; Kashino, S.; Takeuchi, Y.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 833-837. Midura, W. H.; Krysiak, J. A.; Mikolajczyk, M. Tetrahedron 1999, 55, 14791-14802. Priego, J.; Carretero, J. C. Synlett 1999, 1603-1605. Buezo, N. D.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129-7130.
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Krysiak, J.A.2
Mikolajczyk, M.3
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For leading references for reaction of vinylic sulfoxides, see: Mase, N.; Watanabe, Y.; Toru, T.; Kakumoto, T.; Hagiwara, T. J. Org. Chem. 2000, 65, 7083-7090. Maezaki, N.; Izumi, M.; Yuyama, S.; Sawamoto, H.; Iwata, C.; Tanaka, T. Tetrahedron 2000, 56, 7927-7945. Abe, H.; Tsuchida, D.; Kashino, S.; Takeuchi, Y.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 833-837. Midura, W. H.; Krysiak, J. A.; Mikolajczyk, M. Tetrahedron 1999, 55, 14791-14802. Priego, J.; Carretero, J. C. Synlett 1999, 1603-1605. Buezo, N. D.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129-7130.
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Priego, J.1
Carretero, J.C.2
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16
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0032558144
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For leading references for reaction of vinylic sulfoxides, see: Mase, N.; Watanabe, Y.; Toru, T.; Kakumoto, T.; Hagiwara, T. J. Org. Chem. 2000, 65, 7083-7090. Maezaki, N.; Izumi, M.; Yuyama, S.; Sawamoto, H.; Iwata, C.; Tanaka, T. Tetrahedron 2000, 56, 7927-7945. Abe, H.; Tsuchida, D.; Kashino, S.; Takeuchi, Y.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 833-837. Midura, W. H.; Krysiak, J. A.; Mikolajczyk, M. Tetrahedron 1999, 55, 14791-14802. Priego, J.; Carretero, J. C. Synlett 1999, 1603-1605. Buezo, N. D.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129-7130.
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Carretero, J.C.3
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17
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0038401357
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-
note
-
Yields of the bis-sulfinyl alkenes were calculated based on the theoretical maximum 50% yield in this paper.
-
-
-
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18
-
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0037145005
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The diastereomeric isomers were presumably produced by racemization of the introduced sulfoxide via sulfinyl-sulfenate tautomerization (see Scheme 1). However, it is possible to introduce optically pure sulfoxide by using an epimeric mixture of sulfoxide bearing a chiral auxiliary. We have already reported the preliminary results of the asymmetric sulfinylzincation in a recent report. Maezaki, N.; Yagi, S.; Ohsawa, S.; Ohishi, H.; Tanaka, T. Tetrahedron: Asymmetry 2002, 13, 1961-1964.
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Tetrahedron: Asymmetry
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Maezaki, N.1
Yagi, S.2
Ohsawa, S.3
Ohishi, H.4
Tanaka, T.5
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19
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33845282956
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Kosugi, H.; Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. Org. Chem. 1987, 52, 1078-1082.
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Kosugi, H.1
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Tagami, K.3
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Uda, H.5
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20
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-
84855500715
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2(dppf), see: Stadtmüller, H.; Vaupel, A.; Tucker, C. E.; Stüdemann, T.; Knochel, P. Chem. Eur. J. 1996, 2, 1204-1220.
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Stadtmüller, H.1
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Knochel, P.5
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0030037159
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Marsan, M.-P.; Warnock, W.; Muller, I.; Nakatani, Y.; Ourisson, G.; Milon, A. J. Org. Chem. 1996, 61, 4252-4257.
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Ourisson, G.5
Milon, A.6
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22
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0035843313
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The oxidative addition of Pd(0) to the carbon-sulfur bond of the thioalkynes was reported, see: Savarin, C.; Srogel, J.; Liebeskind, L. S. Org. Lett. 2001, 3, 91-93.
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24
-
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0038063057
-
-
note
-
These yields were calculated on the basis of a theoretical maximum 50% yield.
-
-
-
-
25
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0013323218
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Yamamda, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486-4487.
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Tomioka, K.6
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Yamamda, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486-4487.
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0035908165
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Back, T. G. Tetrahedron 2001, 57, 5263-5301 and references therein.
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Back, T.G.1
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28
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0038739538
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note
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All attempts to isolate zinc sulfenate species failed presumably due to its instability.
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29
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0038401355
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Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, UK, and references therein
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Perlmutter, P.1
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