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Volumn 61, Issue 2, 1996, Pages 489-493

Preparation of enantiomerically enriched (2R,3R)- or (2S,3S)-trans-2,3-diaryloxiranes via camphor-derived sulfonium ylides

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE DERIVATIVE;

EID: 0030024622     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951442+     Document Type: Article
Times cited : (116)

References (55)
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    • For a review on Sharpless epoxidations: (a) Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press. Oxford, 1991; Vol. 7, pp 389-436. For Mn salen complex-catalyzed asymmetric epoxidation: (b) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801-2803. For a review on metalloporphyrin-catalyzed asymmetric epoxidation: (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S., Brauman, J. I. Science 1993, 261, 1404-1411. Other methods for asymmetric epoxidation: (d) Koch, A.; Reymond, J.-L.; Lerner, R. A. J Am. Chem. Soc. 1994, 116, 803-804. (e) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc 1993, 115, 4415-4416. (f) Davis, F. A.; Harakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123-3126.
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    • Koch, A.1    Reymond, J.-L.2    Lerner, R.A.3
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    • For a review on Sharpless epoxidations: (a) Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press. Oxford, 1991; Vol. 7, pp 389-436. For Mn salen complex-catalyzed asymmetric epoxidation: (b) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801-2803. For a review on metalloporphyrin-catalyzed asymmetric epoxidation: (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S., Brauman, J. I. Science 1993, 261, 1404-1411. Other methods for asymmetric epoxidation: (d) Koch, A.; Reymond, J.-L.; Lerner, R. A. J Am. Chem. Soc. 1994, 116, 803-804. (e) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc 1993, 115, 4415-4416. (f) Davis, F. A.; Harakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123-3126.
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    • Allain, E.J.1    Hager, L.P.2    Deng, L.3    Jacobsen, E.N.4
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    • For a review on Sharpless epoxidations: (a) Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press. Oxford, 1991; Vol. 7, pp 389-436. For Mn salen complex-catalyzed asymmetric epoxidation: (b) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801-2803. For a review on metalloporphyrin-catalyzed asymmetric epoxidation: (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S., Brauman, J. I. Science 1993, 261, 1404-1411. Other methods for asymmetric epoxidation: (d) Koch, A.; Reymond, J.-L.; Lerner, R. A. J Am. Chem. Soc. 1994, 116, 803-804. (e) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc 1993, 115, 4415-4416. (f) Davis, F. A.; Harakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123-3126.
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    • Asymmetric epoxidation with sulfoximine ylides: (a) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1968, 90, 6852-6854. (b) Johnson, C. R.; Schroeck, C. W. J. Am, Chem. Soc. 1973, 95, 7418-7423. (c) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424-7431. (d) Taj, S. S.; Soman, R. Tetrahedron, Asymmetry 1994, 5, 1513-1518- With arsonium ylides: (e) Allen, D. G.; Roberts, N. K; Wild, S. B. J Chem. Soc., Chem. Commun. 1978, 346-347. (f) Allen, D. G.; Wild, S. B. Organometallics 1983, 2, 394-399. With dimethylsulfonium methylide in the presence of ehiral phasetransfer catalysts: (g) Hiyama, T.; Mishima, T.; Sawada, H.; Nozaki, H. J. Am. Chem. Soc. 1975, 97, 1626-1627. With chiral sulfimides: (h) Baird, C. P.; Taylor, P. C. J. Chem. Soc., Chem. Commun. 1995, 893-894.
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    • Asymmetric epoxidation with sulfoximine ylides: (a) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1968, 90, 6852-6854. (b) Johnson, C. R.; Schroeck, C. W. J. Am, Chem. Soc. 1973, 95, 7418-7423. (c) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424-7431. (d) Taj, S. S.; Soman, R. Tetrahedron, Asymmetry 1994, 5, 1513-1518- With arsonium ylides: (e) Allen, D. G.; Roberts, N. K; Wild, S. B. J Chem. Soc., Chem. Commun. 1978, 346-347. (f) Allen, D. G.; Wild, S. B. Organometallics 1983, 2, 394-399. With dimethylsulfonium methylide in the presence of ehiral phasetransfer catalysts: (g) Hiyama, T.; Mishima, T.; Sawada, H.; Nozaki, H. J. Am. Chem. Soc. 1975, 97, 1626-1627. With chiral sulfimides: (h) Baird, C. P.; Taylor, P. C. J. Chem. Soc., Chem. Commun. 1995, 893-894.
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    • Asymmetric epoxidation with sulfoximine ylides: (a) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1968, 90, 6852-6854. (b) Johnson, C. R.; Schroeck, C. W. J. Am, Chem. Soc. 1973, 95, 7418-7423. (c) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424-7431. (d) Taj, S. S.; Soman, R. Tetrahedron, Asymmetry 1994, 5, 1513-1518- With arsonium ylides: (e) Allen, D. G.; Roberts, N. K; Wild, S. B. J Chem. Soc., Chem. Commun. 1978, 346-347. (f) Allen, D. G.; Wild, S. B. Organometallics 1983, 2, 394-399. With dimethylsulfonium methylide in the presence of ehiral phasetransfer catalysts: (g) Hiyama, T.; Mishima, T.; Sawada, H.; Nozaki, H. J. Am. Chem. Soc. 1975, 97, 1626-1627. With chiral sulfimides: (h) Baird, C. P.; Taylor, P. C. J. Chem. Soc., Chem. Commun. 1995, 893-894.
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    • 0028040777 scopus 로고
    • Asymmetric epoxidation with sulfoximine ylides: (a) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1968, 90, 6852-6854. (b) Johnson, C. R.; Schroeck, C. W. J. Am, Chem. Soc. 1973, 95, 7418-7423. (c) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424-7431. (d) Taj, S. S.; Soman, R. Tetrahedron, Asymmetry 1994, 5, 1513-1518- With arsonium ylides: (e) Allen, D. G.; Roberts, N. K; Wild, S. B. J Chem. Soc., Chem. Commun. 1978, 346-347. (f) Allen, D. G.; Wild, S. B. Organometallics 1983, 2, 394-399. With dimethylsulfonium methylide in the presence of ehiral phasetransfer catalysts: (g) Hiyama, T.; Mishima, T.; Sawada, H.; Nozaki, H. J. Am. Chem. Soc. 1975, 97, 1626-1627. With chiral sulfimides: (h) Baird, C. P.; Taylor, P. C. J. Chem. Soc., Chem. Commun. 1995, 893-894.
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    • Taj, S.S.1    Soman, R.2
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    • Asymmetric epoxidation with sulfoximine ylides: (a) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1968, 90, 6852-6854. (b) Johnson, C. R.; Schroeck, C. W. J. Am, Chem. Soc. 1973, 95, 7418-7423. (c) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424-7431. (d) Taj, S. S.; Soman, R. Tetrahedron, Asymmetry 1994, 5, 1513-1518- With arsonium ylides: (e) Allen, D. G.; Roberts, N. K; Wild, S. B. J Chem. Soc., Chem. Commun. 1978, 346-347. (f) Allen, D. G.; Wild, S. B. Organometallics 1983, 2, 394-399. With dimethylsulfonium methylide in the presence of ehiral phasetransfer catalysts: (g) Hiyama, T.; Mishima, T.; Sawada, H.; Nozaki, H. J. Am. Chem. Soc. 1975, 97, 1626-1627. With chiral sulfimides: (h) Baird, C. P.; Taylor, P. C. J. Chem. Soc., Chem. Commun. 1995, 893-894.
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    • Allen, D.G.1    Roberts, N.K.2    Wild, S.B.3
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    • Asymmetric epoxidation with sulfoximine ylides: (a) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1968, 90, 6852-6854. (b) Johnson, C. R.; Schroeck, C. W. J. Am, Chem. Soc. 1973, 95, 7418-7423. (c) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424-7431. (d) Taj, S. S.; Soman, R. Tetrahedron, Asymmetry 1994, 5, 1513-1518- With arsonium ylides: (e) Allen, D. G.; Roberts, N. K; Wild, S. B. J Chem. Soc., Chem. Commun. 1978, 346-347. (f) Allen, D. G.; Wild, S. B. Organometallics 1983, 2, 394-399. With dimethylsulfonium methylide in the presence of ehiral phasetransfer catalysts: (g) Hiyama, T.; Mishima, T.; Sawada, H.; Nozaki, H. J. Am. Chem. Soc. 1975, 97, 1626-1627. With chiral sulfimides: (h) Baird, C. P.; Taylor, P. C. J. Chem. Soc., Chem. Commun. 1995, 893-894.
    • (1983) Organometallics , vol.2 , pp. 394-399
    • Allen, D.G.1    Wild, S.B.2
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    • Asymmetric epoxidation with sulfoximine ylides: (a) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1968, 90, 6852-6854. (b) Johnson, C. R.; Schroeck, C. W. J. Am, Chem. Soc. 1973, 95, 7418-7423. (c) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424-7431. (d) Taj, S. S.; Soman, R. Tetrahedron, Asymmetry 1994, 5, 1513-1518- With arsonium ylides: (e) Allen, D. G.; Roberts, N. K; Wild, S. B. J Chem. Soc., Chem. Commun. 1978, 346-347. (f) Allen, D. G.; Wild, S. B. Organometallics 1983, 2, 394-399. With dimethylsulfonium methylide in the presence of ehiral phasetransfer catalysts: (g) Hiyama, T.; Mishima, T.; Sawada, H.; Nozaki, H. J. Am. Chem. Soc. 1975, 97, 1626-1627. With chiral sulfimides: (h) Baird, C. P.; Taylor, P. C. J. Chem. Soc., Chem. Commun. 1995, 893-894.
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    • Hiyama, T.1    Mishima, T.2    Sawada, H.3    Nozaki, H.4
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    • Asymmetric epoxidation with sulfoximine ylides: (a) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1968, 90, 6852-6854. (b) Johnson, C. R.; Schroeck, C. W. J. Am, Chem. Soc. 1973, 95, 7418-7423. (c) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424-7431. (d) Taj, S. S.; Soman, R. Tetrahedron, Asymmetry 1994, 5, 1513-1518- With arsonium ylides: (e) Allen, D. G.; Roberts, N. K; Wild, S. B. J Chem. Soc., Chem. Commun. 1978, 346-347. (f) Allen, D. G.; Wild, S. B. Organometallics 1983, 2, 394-399. With dimethylsulfonium methylide in the presence of ehiral phasetransfer catalysts: (g) Hiyama, T.; Mishima, T.; Sawada, H.; Nozaki, H. J. Am. Chem. Soc. 1975, 97, 1626-1627. With chiral sulfimides: (h) Baird, C. P.; Taylor, P. C. J. Chem. Soc., Chem. Commun. 1995, 893-894.
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    • note
    • 10


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.