메뉴 건너뛰기




Volumn , Issue 4, 2004, Pages 643-646

Phase transfer catalysed asymmetric epoxidation of chalcones using chiral crown ethers derived from D-glucose and D-mannose

Author keywords

Asymmetric epoxidation; Asymmetric phase transfer catalysis; Chiral crown ethers; Lariate ether

Indexed keywords

CHALCONE DERIVATIVE; CROWN ETHER DERIVATIVE; GLUCOSE; MANNOSE; TERT BUTYL HYDROPEROXIDE;

EID: 1642320895     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817751     Document Type: Article
Times cited : (41)

References (23)
  • 4
    • 33748048522 scopus 로고    scopus 로고
    • and references cited therein
    • (b) Miethchen, R.; Fehring, V. Synthesis 1998, 94; and references cited therein.
    • (1998) Synthesis , pp. 94
    • Miethchen, R.1    Fehring, V.2
  • 8
    • 0032874208 scopus 로고    scopus 로고
    • For recent review, see: (a) Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145. (b) Banfi, S.; Colonna, S.; Molinari, H.; Juliá, S.; Guixer, J. Tetrahedron 1984, 40, 5207. (c) Lygo, B.; Wainwright, P. G. Tetrahedron 1999, 55, 6289. (d) Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287. (e) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563. (f) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725. (g) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959. (h) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666. (i) Watanabe, S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. J. Org. Chem. 1998, 63, 8090.
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 2145
    • Porter, M.J.1    Roberts, S.M.2    Skidmore, J.3
  • 9
    • 0141578843 scopus 로고
    • For recent review, see: (a) Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145. (b) Banfi, S.; Colonna, S.; Molinari, H.; Juliá, S.; Guixer, J. Tetrahedron 1984, 40, 5207. (c) Lygo, B.; Wainwright, P. G. Tetrahedron 1999, 55, 6289. (d) Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287. (e) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563. (f) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725. (g) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959. (h) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666. (i) Watanabe, S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. J. Org. Chem. 1998, 63, 8090.
    • (1984) Tetrahedron , vol.40 , pp. 5207
    • Banfi, S.1    Colonna, S.2    Molinari, H.3    Juliá, S.4    Guixer, J.5
  • 10
    • 0033553370 scopus 로고    scopus 로고
    • For recent review, see: (a) Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145. (b) Banfi, S.; Colonna, S.; Molinari, H.; Juliá, S.; Guixer, J. Tetrahedron 1984, 40, 5207. (c) Lygo, B.; Wainwright, P. G. Tetrahedron 1999, 55, 6289. (d) Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287. (e) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563. (f) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725. (g) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959. (h) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666. (i) Watanabe, S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. J. Org. Chem. 1998, 63, 8090.
    • (1999) Tetrahedron , vol.55 , pp. 6289
    • Lygo, B.1    Wainwright, P.G.2
  • 11
    • 0033592480 scopus 로고    scopus 로고
    • For recent review, see: (a) Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145. (b) Banfi, S.; Colonna, S.; Molinari, H.; Juliá, S.; Guixer, J. Tetrahedron 1984, 40, 5207. (c) Lygo, B.; Wainwright, P. G. Tetrahedron 1999, 55, 6289. (d) Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287. (e) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563. (f) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725. (g) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959. (h) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666. (i) Watanabe, S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. J. Org. Chem. 1998, 63, 8090.
    • (1999) Org. Lett. , vol.1 , pp. 1287
    • Corey, E.J.1    Zhang, F.-Y.2
  • 12
    • 0032497664 scopus 로고    scopus 로고
    • For recent review, see: (a) Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145. (b) Banfi, S.; Colonna, S.; Molinari, H.; Juliá, S.; Guixer, J. Tetrahedron 1984, 40, 5207. (c) Lygo, B.; Wainwright, P. G. Tetrahedron 1999, 55, 6289. (d) Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287. (e) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563. (f) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725. (g) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959. (h) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666. (i) Watanabe, S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. J. Org. Chem. 1998, 63, 8090.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7563
    • Arai, S.1    Tsuge, H.2    Shioiri, T.3
  • 13
    • 0029785064 scopus 로고    scopus 로고
    • For recent review, see: (a) Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145. (b) Banfi, S.; Colonna, S.; Molinari, H.; Juliá, S.; Guixer, J. Tetrahedron 1984, 40, 5207. (c) Lygo, B.; Wainwright, P. G. Tetrahedron 1999, 55, 6289. (d) Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287. (e) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563. (f) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725. (g) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959. (h) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666. (i) Watanabe, S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. J. Org. Chem. 1998, 63, 8090.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1725
    • Enders, D.1    Zhu, J.2    Raabe, G.3
  • 14
    • 0032573443 scopus 로고    scopus 로고
    • For recent review, see: (a) Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145. (b) Banfi, S.; Colonna, S.; Molinari, H.; Juliá, S.; Guixer, J. Tetrahedron 1984, 40, 5207. (c) Lygo, B.; Wainwright, P. G. Tetrahedron 1999, 55, 6289. (d) Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287. (e) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563. (f) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725. (g) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959. (h) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666. (i) Watanabe, S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. J. Org. Chem. 1998, 63, 8090.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3959
    • Enders, D.1    Kramps, L.2    Zhu, J.3
  • 15
    • 0000429727 scopus 로고    scopus 로고
    • For recent review, see: (a) Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145. (b) Banfi, S.; Colonna, S.; Molinari, H.; Juliá, S.; Guixer, J. Tetrahedron 1984, 40, 5207. (c) Lygo, B.; Wainwright, P. G. Tetrahedron 1999, 55, 6289. (d) Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287. (e) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563. (f) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725. (g) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959. (h) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666. (i) Watanabe, S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. J. Org. Chem. 1998, 63, 8090.
    • (1998) J. Org. Chem. , vol.63 , pp. 3666
    • Yamada, K.1    Arai, T.2    Sasai, H.3    Shibasaki, M.4
  • 16
    • 0032514846 scopus 로고    scopus 로고
    • For recent review, see: (a) Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145. (b) Banfi, S.; Colonna, S.; Molinari, H.; Juliá, S.; Guixer, J. Tetrahedron 1984, 40, 5207. (c) Lygo, B.; Wainwright, P. G. Tetrahedron 1999, 55, 6289. (d) Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287. (e) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563. (f) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725. (g) Enders, D.; Kramps, L.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3959. (h) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666. (i) Watanabe, S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. J. Org. Chem. 1998, 63, 8090.
    • (1998) J. Org. Chem. , vol.63 , pp. 8090
    • Watanabe, S.1    Arai, T.2    Sasai, H.3    Bougauchi, M.4    Shibasaki, M.5
  • 22
    • 1642395484 scopus 로고    scopus 로고
    • note
    • + + Na].
  • 23
    • 1642293028 scopus 로고    scopus 로고
    • note
    • 1H NMR: δ = 7.96 (d, 2 H, o-COPh-H), 7.46 (d, 2 H, m-COPh-H), 7.40 (t, 3 H, m,p-CHPh-H), 7.36 (d, 2H, o-CHPh-H), 4.23 (d, J = 1.6 Hz, 1 H, COCH), 4.07 (d, J = 1.3 Hz, 1 H, PhCH).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.