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Volumn 68, Issue 14, 2003, Pages 5550-5558

Pd-catalyzed sulfinylzincation of activated alkynes with 1-alkynyl sulfoxides as a sulfinyl source

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATED ALKYNES;

EID: 0037662080     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034108j     Document Type: Article
Times cited : (29)

References (29)
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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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    • 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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    • 0032822797 scopus 로고    scopus 로고
    • 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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    • note
    • Yields of the bis-sulfinyl alkenes were calculated based on the theoretical maximum 50% yield in this paper.
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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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    • 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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    • note
    • These yields were calculated on the basis of a theoretical maximum 50% yield.
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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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    • and references therein
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    • note
    • All attempts to isolate zinc sulfenate species failed presumably due to its instability.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.