메뉴 건너뛰기




Volumn , Issue 9, 2000, Pages 1711-1718

The effect of the carbon ligand on the reaction of organozinc reagents in the synthesis of substituted 2,5-dihydrofurans: A rare example of an uncatalysed allylic-substitution reaction involving alkyl zinc halides

Author keywords

Catalysts; Heterocycles; Palladium; Sulfur; Zinc

Indexed keywords

CARBON; FURAN DERIVATIVE; HALIDE; ORGANOMETALLIC COMPOUND; PALLADIUM COMPLEX; SULFUR; ZINC DERIVATIVE;

EID: 0034078740     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200005)2000:9<1711::aid-ejoc1711>3.0.co;2-1     Document Type: Article
Times cited : (21)

References (37)
  • 6
    • 0002653770 scopus 로고
    • N. S. Simpkins, Sulphones in Organic Synthesis. Pergamon, Oxford, 1993; B. M. Trost; Bull. Chem. Soc. Jpn. 1988, 61, 107-124.
    • (1988) Bull. Chem. Soc. Jpn. , vol.61 , pp. 107-124
    • Trost, B.M.1
  • 7
    • 0026458587 scopus 로고
    • For reviews of organozinc chemistry see: [5a] E. Erdik, Tetrahedron 1992, 48, 9577-9648. -
    • (1992) Tetrahedron , vol.48 , pp. 9577-9648
    • Erdik, E.1
  • 8
    • 0003779363 scopus 로고    scopus 로고
    • (Eds.: M. Beller and C. Bolm), Wiley-VCH, Weinheim
    • [5b] P. Knochel, in Transition Metals for Organic Synthesis (Eds.: M. Beller and C. Bolm), Wiley-VCH, Weinheim, 1998, Vol 1, p. 467. -
    • (1998) Transition Metals for Organic Synthesis , vol.1 , pp. 467
    • Knochel, P.1
  • 9
    • 0001986650 scopus 로고    scopus 로고
    • (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim
    • [5c] P. Knochel, in Metal-catalysed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, p. 387.
    • (1998) Metal-catalysed Cross-coupling Reactions , pp. 387
    • Knochel, P.1
  • 15
    • 0028016057 scopus 로고
    • M. V. Hanson, J. D. Brown, R. D. Rieke, Q. J. Niu, Tetrahedron Lett. 1994, 35, 7205-7208; R. D. Rieke, M. V. Hanson, J. D. Brown, Q. J. Niu, J. Org. Chem. 1996, 61, 2726-2730; A. Guijarro, D. M. Rosenberg, R. D. Rieke, J. Am. Chem. Soc. 1999, 121, 4155-4167.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7205-7208
    • Hanson, M.V.1    Brown, J.D.2    Rieke, R.D.3    Niu, Q.J.4
  • 16
    • 0000618905 scopus 로고    scopus 로고
    • M. V. Hanson, J. D. Brown, R. D. Rieke, Q. J. Niu, Tetrahedron Lett. 1994, 35, 7205-7208; R. D. Rieke, M. V. Hanson, J. D. Brown, Q. J. Niu, J. Org. Chem. 1996, 61, 2726-2730; A. Guijarro, D. M. Rosenberg, R. D. Rieke, J. Am. Chem. Soc. 1999, 121, 4155-4167.
    • (1996) J. Org. Chem. , vol.61 , pp. 2726-2730
    • Rieke, R.D.1    Hanson, M.V.2    Brown, J.D.3    Niu, Q.J.4
  • 17
    • 0033526370 scopus 로고    scopus 로고
    • M. V. Hanson, J. D. Brown, R. D. Rieke, Q. J. Niu, Tetrahedron Lett. 1994, 35, 7205-7208; R. D. Rieke, M. V. Hanson, J. D. Brown, Q. J. Niu, J. Org. Chem. 1996, 61, 2726-2730; A. Guijarro, D. M. Rosenberg, R. D. Rieke, J. Am. Chem. Soc. 1999, 121, 4155-4167.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 4155-4167
    • Guijarro, A.1    Rosenberg, D.M.2    Rieke, R.D.3
  • 18
    • 0025907487 scopus 로고
    • D. Villemin, A. B. Alloum, Synth. Commun. 1991, 21, 63-68; G. R. Reddy, S. V. S. A. K. Gupta, D. B. Reddy, B. Seenaiah, J. Indian Chem. Soc. 1992, 69, 396-397.
    • (1991) Synth. Commun. , vol.21 , pp. 63-68
    • Villemin, D.1    Alloum, A.B.2
  • 22
    • 0000971680 scopus 로고
    • H. Matsushita, E.-I Negishi, J. Am. Chem. Soc. 1981, 103, 2882-2884; T. Hayashi, A. Yamamoto, T. Hagihara, J. Org. Chem. 1986, 51, 723-727; H. Matsushita, S. Chatterjee, E.-I. Negishi, Tetrahedron Lett. 1981, 22, 3737-3740.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 2882-2884
    • Matsushita, H.1    Negishi, E.-I.2
  • 23
    • 0001124147 scopus 로고
    • H. Matsushita, E.-I Negishi, J. Am. Chem. Soc. 1981, 103, 2882-2884; T. Hayashi, A. Yamamoto, T. Hagihara, J. Org. Chem. 1986, 51, 723-727; H. Matsushita, S. Chatterjee, E.-I. Negishi, Tetrahedron Lett. 1981, 22, 3737-3740.
    • (1986) J. Org. Chem. , vol.51 , pp. 723-727
    • Hayashi, T.1    Yamamoto, A.2    Hagihara, T.3
  • 24
    • 0001682179 scopus 로고
    • H. Matsushita, E.-I Negishi, J. Am. Chem. Soc. 1981, 103, 2882-2884; T. Hayashi, A. Yamamoto, T. Hagihara, J. Org. Chem. 1986, 51, 723-727; H. Matsushita, S. Chatterjee, E.-I. Negishi, Tetrahedron Lett. 1981, 22, 3737-3740.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3737-3740
    • Matsushita, H.1    Chatterjee, S.2    Negishi, E.-I.3
  • 25
    • 0025353115 scopus 로고
    • E.-I. Negishi, Y. Noda, F. Lamaty, E. J. Vauter, Tetrahedron Lett. 1990, 31, 4393-4396; M. Rottländer, P. Knochel, Tetrahedron Lett. 1997, 38, 1749-1752; Y. Nakamura, M. Matsumoto, Y. Hayashida, J. Nishimura, Tetrahedron Lett. 1997, 38, 1983-1986.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 4393-4396
    • Negishi, E.-I.1    Noda, Y.2    Lamaty, F.3    Vauter, E.J.4
  • 26
    • 0031562385 scopus 로고    scopus 로고
    • E.-I. Negishi, Y. Noda, F. Lamaty, E. J. Vauter, Tetrahedron Lett. 1990, 31, 4393-4396; M. Rottländer, P. Knochel, Tetrahedron Lett. 1997, 38, 1749-1752; Y. Nakamura, M. Matsumoto, Y. Hayashida, J. Nishimura, Tetrahedron Lett. 1997, 38, 1983-1986.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1749-1752
    • Rottländer, M.1    Knochel, P.2
  • 27
    • 0031575732 scopus 로고    scopus 로고
    • E.-I. Negishi, Y. Noda, F. Lamaty, E. J. Vauter, Tetrahedron Lett. 1990, 31, 4393-4396; M. Rottländer, P. Knochel, Tetrahedron Lett. 1997, 38, 1749-1752; Y. Nakamura, M. Matsumoto, Y. Hayashida, J. Nishimura, Tetrahedron Lett. 1997, 38, 1983-1986.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1983-1986
    • Nakamura, Y.1    Matsumoto, M.2    Hayashida, Y.3    Nishimura, J.4
  • 28
    • 0008526034 scopus 로고
    • The importance of the magnesium salts in this reaction is also supported by the observation that when the allylic sulfone 3 is treated with diethyl zinc only traces of the substituted 2,5-dihydrofuran are obtained
    • M. Julia, M. Nel, D. Uguen, Bull. Soc. Chim. Fr. 1987, 487-492; The importance of the magnesium salts in this reaction is also supported by the observation that when the allylic sulfone 3 is treated with diethyl zinc only traces of the substituted 2,5-dihydrofuran are obtained.
    • (1987) Bull. Soc. Chim. Fr. , pp. 487-492
    • Julia, M.1    Nel, M.2    Uguen, D.3
  • 33
    • 0000061909 scopus 로고
    • E. Keinan, Z. Roth, J. Org. Chem. 1983, 48, 1769-1772; E. Keinan, M. Peretz, J. Org. Chem. 1983, 48, 5302-5309; S. Torii, H. Tanaka, T. Katch, K. Morisaki, Tetrahedron Lett. 1984, 25, 3207-3208.
    • (1983) J. Org. Chem. , vol.48 , pp. 1769-1772
    • Keinan, E.1    Roth, Z.2
  • 34
    • 5244243008 scopus 로고
    • E. Keinan, Z. Roth, J. Org. Chem. 1983, 48, 1769-1772; E. Keinan, M. Peretz, J. Org. Chem. 1983, 48, 5302-5309; S. Torii, H. Tanaka, T. Katch, K. Morisaki, Tetrahedron Lett. 1984, 25, 3207-3208.
    • (1983) J. Org. Chem. , vol.48 , pp. 5302-5309
    • Keinan, E.1    Peretz, M.2
  • 35
    • 0000177152 scopus 로고
    • E. Keinan, Z. Roth, J. Org. Chem. 1983, 48, 1769-1772; E. Keinan, M. Peretz, J. Org. Chem. 1983, 48, 5302-5309; S. Torii, H. Tanaka, T. Katch, K. Morisaki, Tetrahedron Lett. 1984, 25, 3207-3208.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 3207-3208
    • Torii, S.1    Tanaka, H.2    Katch, T.3    Morisaki, K.4
  • 36
    • 0342275742 scopus 로고    scopus 로고
    • note
    • All attempts to incorporate other electrophiles proved unsuccessful with the starting sulfone 3 recovered in quantitative yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.