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Volumn 44, Issue 45, 2003, Pages 8253-8256

Synthesis of tetrahydrofurans via silicon promoted Pummerer type reaction

Author keywords

Pummerer rearrangement; Sulfoxide; t butyldiphenylchlorosilane; Tetrahydrofurans

Indexed keywords

CARBON; SULFOXIDE; TETRAHYDROFURAN DERIVATIVE;

EID: 0141922949     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.062     Document Type: Article
Times cited : (7)

References (24)
  • 5
    • 0001272894 scopus 로고
    • Paquette, L. A., Ed.; Wiley: New York; Chapter 3
    • De Lucchi, O.; Miotti, U.; Modena, G. Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1991; Chapter 3, pp. 157-184.
    • (1991) Organic Reactions , pp. 157-184
    • De Lucchi, O.1    Miotti, U.2    Modena, G.3
  • 11
    • 0013121740 scopus 로고
    • Kersey, I. D.; Fishwick, C. W. G.; Findlay, J. B. C.; Ward, P. Tetrahedron 1995, 51, 6819. Also refer to: Tokitoh, N.; Igarashi, Y.; Ando, W. Tetrahedron Lett. 1987, 28, 5903.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5903
    • Tokitoh, N.1    Igarashi, Y.2    Ando, W.3
  • 12
    • 0012674512 scopus 로고
    • For the preparation of lactones by Pummerer type reaction, refer to: Su, H.; Hiwatari, Y.; Soenosawa, M.; Sasuga, K.; Shirai, K.; Kumamoto, T. Bull. Chem. Soc. Jpn. 1993, 66, 2603. For the preparation of lactams refer to: (a) Iwao, M. Heterocycles 1994, 38, 45; (b) Kaneko, T. J. Am. Chem. Soc. 1985, 107, 5490; (c) Kita, Y.; Shibata, N. Synlett 1996, 289; (d) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115. For the synthesis of dihydrofurans/furans, refer to: Chan, W. H.; Lee, A. W. M.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 945.
    • (1993) Bull. Chem. Soc. Jpn. , vol.66 , pp. 2603
    • Su, H.1    Hiwatari, Y.2    Soenosawa, M.3    Sasuga, K.4    Shirai, K.5    Kumamoto, T.6
  • 13
    • 0002048021 scopus 로고
    • For the preparation of lactones by Pummerer type reaction, refer to: Su, H.; Hiwatari, Y.; Soenosawa, M.; Sasuga, K.; Shirai, K.; Kumamoto, T. Bull. Chem. Soc. Jpn. 1993, 66, 2603. For the preparation of lactams refer to: (a) Iwao, M. Heterocycles 1994, 38, 45; (b) Kaneko, T. J. Am. Chem. Soc. 1985, 107, 5490; (c) Kita, Y.; Shibata, N. Synlett 1996, 289; (d) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115. For the synthesis of dihydrofurans/furans, refer to: Chan, W. H.; Lee, A. W. M.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 945.
    • (1994) Heterocycles , vol.38 , pp. 45
    • Iwao, M.1
  • 14
    • 0021997094 scopus 로고
    • For the preparation of lactones by Pummerer type reaction, refer to: Su, H.; Hiwatari, Y.; Soenosawa, M.; Sasuga, K.; Shirai, K.; Kumamoto, T. Bull. Chem. Soc. Jpn. 1993, 66, 2603. For the preparation of lactams refer to: (a) Iwao, M. Heterocycles 1994, 38, 45; (b) Kaneko, T. J. Am. Chem. Soc. 1985, 107, 5490; (c) Kita, Y.; Shibata, N. Synlett 1996, 289; (d) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115. For the synthesis of dihydrofurans/furans, refer to: Chan, W. H.; Lee, A. W. M.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 945.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 5490
    • Kaneko, T.1
  • 15
    • 0039240357 scopus 로고    scopus 로고
    • For the preparation of lactones by Pummerer type reaction, refer to: Su, H.; Hiwatari, Y.; Soenosawa, M.; Sasuga, K.; Shirai, K.; Kumamoto, T. Bull. Chem. Soc. Jpn. 1993, 66, 2603. For the preparation of lactams refer to: (a) Iwao, M. Heterocycles 1994, 38, 45; (b) Kaneko, T. J. Am. Chem. Soc. 1985, 107, 5490; (c) Kita, Y.; Shibata, N. Synlett 1996, 289; (d) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115. For the synthesis of dihydrofurans/furans, refer to: Chan, W. H.; Lee, A. W. M.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 945.
    • (1996) Synlett , pp. 289
    • Kita, Y.1    Shibata, N.2
  • 16
    • 0028891046 scopus 로고
    • For the preparation of lactones by Pummerer type reaction, refer to: Su, H.; Hiwatari, Y.; Soenosawa, M.; Sasuga, K.; Shirai, K.; Kumamoto, T. Bull. Chem. Soc. Jpn. 1993, 66, 2603. For the preparation of lactams refer to: (a) Iwao, M. Heterocycles 1994, 38, 45; (b) Kaneko, T. J. Am. Chem. Soc. 1985, 107, 5490; (c) Kita, Y.; Shibata, N. Synlett 1996, 289; (d) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115. For the synthesis of dihydrofurans/furans, refer to: Chan, W. H.; Lee, A. W. M.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 945.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 115
    • Kita, Y.1    Shibata, N.2    Kawano, N.3    Tohjo, T.4    Matsumoto, K.5
  • 17
    • 37049066879 scopus 로고
    • For the preparation of lactones by Pummerer type reaction, refer to: Su, H.; Hiwatari, Y.; Soenosawa, M.; Sasuga, K.; Shirai, K.; Kumamoto, T. Bull. Chem. Soc. Jpn. 1993, 66, 2603. For the preparation of lactams refer to: (a) Iwao, M. Heterocycles 1994, 38, 45; (b) Kaneko, T. J. Am. Chem. Soc. 1985, 107, 5490; (c) Kita, Y.; Shibata, N. Synlett 1996, 289; (d) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115. For the synthesis of dihydrofurans/furans, refer to: Chan, W. H.; Lee, A. W. M.; Chan, E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 945.
    • (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 945
    • Chan, W.H.1    Lee, A.W.M.2    Chan, E.T.T.3
  • 22
    • 85031050724 scopus 로고    scopus 로고
    • 4. The solvent was evaporated under reduced pressure to afford the crude product mixture. Purification by column chromatography using EtOAc:hexane (1:24) afforded the pure product
    • 4. The solvent was evaporated under reduced pressure to afford the crude product mixture. Purification by column chromatography using EtOAc:hexane (1:24) afforded the pure product.
  • 24
    • 0036007699 scopus 로고    scopus 로고
    • Brown, D. S.; Bruno, M.; Davenport, R. J.; Ley. S. V. Tetrahedron 1989, 45, 4293. Review: Chemla, F. J. Chem. Soc., Perkin Trans. 1 2002, 275.
    • (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 275
    • Chemla, F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.