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Volumn 37, Issue 16, 1998, Pages 2223-2226

Enantioselective ring opening of epoxides with 4-methoxyphenol catalyzed by gallium heterobimetallic complexes: An efficient method for the synthesis of optically active 1,2-diol monoethers

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Epoxides; Gallium; Oxygen nucleophiles

Indexed keywords


EID: 0031704998     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980904)37:16<2223::AID-ANIE2223>3.0.CO;2-Z     Document Type: Article
Times cited : (111)

References (33)
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    • For an alternative approach to the synthesis of optically active 1,2-diols by the catalytic asymmetric dihydoxylations of olefins, which was realized by K. B. Sharpless et al., see H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
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    • Kolb, H.C.1    VanNieuwenhze, M.S.2    Sharpless, K.B.3
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    • note
    • The product from the ring opening of 3 with binaphthol was obtained in 24% yield (based on binaphthol).
  • 10
    • 0345334978 scopus 로고    scopus 로고
    • note
    • [19] and 4,4′-dibromo-or dimethylbinaphthol gave less satisfactory results.
  • 11
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    • Another application of 6,6′-bis((trialkylsilyl)ethynyl)-binaphthol is in catalytic asymmetric nitroaldol reactions: a) H. Sasai, T. Tokunaga, S. Watanabe, T. Suzuki, N. Itoh, M. Shibasaki, J. Org. Chem. 1995, 23, 7388-7389; b) E. Takaoka, N. Yoshikawa, Y. M. A. Yamada, H. Sasai, M. Shibasaki, Heterocycles 1997, 46, 157-163.
    • (1995) J. Org. Chem. , vol.23 , pp. 7388-7389
    • Sasai, H.1    Tokunaga, T.2    Watanabe, S.3    Suzuki, T.4    Itoh, N.5    Shibasaki, M.6
  • 12
    • 0000042562 scopus 로고    scopus 로고
    • Another application of 6,6′-bis((trialkylsilyl)ethynyl)-binaphthol is in catalytic asymmetric nitroaldol reactions: a) H. Sasai, T. Tokunaga, S. Watanabe, T. Suzuki, N. Itoh, M. Shibasaki, J. Org. Chem. 1995, 23, 7388-7389; b) E. Takaoka, N. Yoshikawa, Y. M. A. Yamada, H. Sasai, M. Shibasaki, Heterocycles 1997, 46, 157-163.
    • (1997) Heterocycles , vol.46 , pp. 157-163
    • Takaoka, E.1    Yoshikawa, N.2    Yamada, Y.M.A.3    Sasai, H.4    Shibasaki, M.5
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    • For a review on heterobimetallic catalysts, see a) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1310; Angew. Chem. Int. Ed Engl. 1997, 36, 1236-1256; b) H. Steinhagen, G. Helmchen, Angew. Chem. 1996, 108, 2489-2492; Angew. Chem. Int. Ed. Engl. 1996, 35, 2339-2342.
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    • Shibasaki, M.1    Sasai, H.2    Arai, T.3
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    • 0030788440 scopus 로고    scopus 로고
    • For a review on heterobimetallic catalysts, see a) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1310; Angew. Chem. Int. Ed Engl. 1997, 36, 1236-1256; b) H. Steinhagen, G. Helmchen, Angew. Chem. 1996, 108, 2489-2492; Angew. Chem. Int. Ed. Engl. 1996, 35, 2339-2342.
    • (1997) Angew. Chem. Int. Ed Engl. , vol.36 , pp. 1236-1256
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    • For a review on heterobimetallic catalysts, see a) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1310; Angew. Chem. Int. Ed Engl. 1997, 36, 1236-1256; b) H. Steinhagen, G. Helmchen, Angew. Chem. 1996, 108, 2489-2492; Angew. Chem. Int. Ed. Engl. 1996, 35, 2339-2342.
    • (1996) Angew. Chem. , vol.108 , pp. 2489-2492
    • Steinhagen, H.1    Helmchen, G.2
  • 16
    • 0030472830 scopus 로고    scopus 로고
    • For a review on heterobimetallic catalysts, see a) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1310; Angew. Chem. Int. Ed Engl. 1997, 36, 1236-1256; b) H. Steinhagen, G. Helmchen, Angew. Chem. 1996, 108, 2489-2492; Angew. Chem. Int. Ed. Engl. 1996, 35, 2339-2342.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2339-2342
  • 17
    • 0344903805 scopus 로고    scopus 로고
    • note
    • [22] (20% yield, 72% ee) gave much less satisfactory results.
  • 18
    • 0345334975 scopus 로고    scopus 로고
    • note
    • [25] gave unsatisfactory results.
  • 20
    • 0030952111 scopus 로고    scopus 로고
    • 8-binaphthoxide) complex see: a) A. S. C. Chan, F.-Y. Zhang, C.-W. Yip, J. Am. Chem. Soc. 1997, 119, 4080-4081; b) F.-Y. Zhang, A. S. C. Chan, Tetrahedron: Asymmetry, 1997, 8, 3651-3655.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 4080-4081
    • Chan, A.S.C.1    Zhang, F.-Y.2    Yip, C.-W.3
  • 21
    • 0031566717 scopus 로고    scopus 로고
    • 8-binaphthoxide) complex see: a) A. S. C. Chan, F.-Y. Zhang, C.-W. Yip, J. Am. Chem. Soc. 1997, 119, 4080-4081; b) F.-Y. Zhang, A. S. C. Chan, Tetrahedron: Asymmetry, 1997, 8, 3651-3655.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 3651-3655
    • Zhang, F.-Y.1    Chan, A.S.C.2
  • 22
    • 0345334974 scopus 로고    scopus 로고
    • note
    • 71Ga).
  • 23
    • 0344041072 scopus 로고    scopus 로고
    • note
    • 8-binaphthoxide) (58% yield, 52% ee) gave less satisfactory results.
  • 27
    • 0344041070 scopus 로고    scopus 로고
    • note
    • 3 (1 mmol), 1,1′-(R)-binaphthol (2 mmol), and nBuLi (3 mmol) in THF at room temperature.
  • 29
    • 33748240969 scopus 로고    scopus 로고
    • T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki, Angew. Chem. 1996, 108, 103-105; Angew. Chem. Int. Ed. Engl. 1996, 35, 104-106.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 104-106


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.