Asymmetric ylide reactions: Epoxidation, cyclopropanation, aziridination, olefination, and rearrangement

Chemical Reviews

Volumn 97, Issue 6, 1997, Pages 2341-2372

  Li, An Hu ^a   Dai, Li Xin ^a   Aggarwal, Varinder K ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001485086     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr960411r     Document Type: Article

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58. 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. For chiral ketone-mediated asymmetric epoxidation: (c) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. For metalloporphyrin-catalyzed asymmetric epoxidation: (f) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. Other methods for asymmetric epoxidation: (g) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803. (h) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415. (i) Davis, F. A.; Karakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123.
59. 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. For chiral ketone-mediated asymmetric epoxidation: (c) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. For metalloporphyrin-catalyzed asymmetric epoxidation: (f) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. Other methods for asymmetric epoxidation: (g) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803. (h) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415. (i) Davis, F. A.; Karakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123.
60. 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. For chiral ketone-mediated asymmetric epoxidation: (c) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. For metalloporphyrin-catalyzed asymmetric epoxidation: (f) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. Other methods for asymmetric epoxidation: (g) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803. (h) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415. (i) Davis, F. A.; Karakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123.
61. 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. For chiral ketone-mediated asymmetric epoxidation: (c) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. For metalloporphyrin-catalyzed asymmetric epoxidation: (f) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. Other methods for asymmetric epoxidation: (g) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803. (h) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415. (i) Davis, F. A.; Karakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123.
62. 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. For chiral ketone-mediated asymmetric epoxidation: (c) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491. (d) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (e) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. For metalloporphyrin-catalyzed asymmetric epoxidation: (f) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. Other methods for asymmetric epoxidation: (g) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803. (h) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415. (i) Davis, F. A.; Karakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123.
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