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Bulletin of the Chemical Society of Japan

Volumn 76, Issue 1, 2003, Pages 189-199

Asymmetric cyclopropanation and aziridination reactions of olefins catalyzed by Cu(I)-binaphthyldiimine complexes

(7) Suga, Hiroyuki a Kakehi, Akikazu a Ito, Suketaka a Ibata, Toshikazu b Fudo, Tomomi b Watanabe, Yuzuru a Kinoshita, Yoshinori a

a SHINSHU UNIVERSITY (Japan)

b OSAKA UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; REACTION KINETICS; SUBSTITUTION REACTIONS;

AZIRIDINATION REACTIONS;

OLEFINS;

ACETIC ACID DERIVATIVE; ACRYLIC ACID DERIVATIVE; ALKENE; AZIRIDINE; COPPER BINAPHTHYLDIIMINE COMPLEX; COPPER COMPLEX; CYCLOPROPANE; IODINE DERIVATIVE; KETONE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; CYCLOPROPANATION; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 0037251239 PISSN: 00092673 EISSN: None Source Type: Journal
DOI: 10.1246/bcsj.76.189 Document Type: Article

Times cited : (45)

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- Asymmetric aziridination using PhI=NTs: a) D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991). b) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson, and D. M. Barnes, J. Am. Chem. Soc., 115, 5328 (1993). c) Z. Li, K. R. Conser, and E. N. Jacobsen, J. Am. Chem. Soc., 115, 5326 (1993). d) W. Zhang, N. H. Lee, and E. N. Jacobsen, J. Am. Chem. Soc., 116, 425 (1994). e) Z. Li, R. W. Quan, and E. N. Jacobsen, J. Am. Chem. Soc., 117, 5889 (1995). f) K. Noda, H. Hosoya, R. Irie, Y. Ito, and T. Katsuki, Synlett, 1993, 469. g) H. Nishikori and T. Katsuki, Tetrahedron Lett., 37, 9245 (1996). h) R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 32, 7373 (1991). i) D. Tanner, P. G. Anderson, A. Harden, and P. Somfai, Tetrahedron Lett., 35, 4631 (1994). j) A. M. Harm, J. G. Knight, and G. Stemp, Synlett, 1996, 677. k) T.-S. Lai, H.-L. Kwong, C.-M. Che, and S.-M. Peng, Chem. Commun., 1997, 2373. l) M. J. Södergren, D. A. Alonso, and P. G. Andersson, Tetrahedron: Asymmetry, 8, 3563 (1997). m) P. Müller, C. Baud, Y. Jacquier, M. Moran, and I. Nägeri, J. Phys. Org. Chem., 9, 341 (1996). R. S. Atkinson, W. T. Gattrell, A. P. Ayscough, and T. M. Raynham, Chem. Commun., 1996, 1935. Asymmetric aziridination usig chiral nitridomanganese complexes: o) S. Minakata, T. Ando, M. Nishimura, I. Ryu, and M. Komatsu, Chem. Commun., 1998, 3392. p) M. Nishimura, S. Minakata, T. Takahashi, Y. Oderaotoshi, and M. Komatsu, J. Org. Chem., 67, 2101 (2002).
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61
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- Asymmetric aziridination using PhI=NTs: a) D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991). b) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson, and D. M. Barnes, J. Am. Chem. Soc., 115, 5328 (1993). c) Z. Li, K. R. Conser, and E. N. Jacobsen, J. Am. Chem. Soc., 115, 5326 (1993). d) W. Zhang, N. H. Lee, and E. N. Jacobsen, J. Am. Chem. Soc., 116, 425 (1994). e) Z. Li, R. W. Quan, and E. N. Jacobsen, J. Am. Chem. Soc., 117, 5889 (1995). f) K. Noda, H. Hosoya, R. Irie, Y. Ito, and T. Katsuki, Synlett, 1993, 469. g) H. Nishikori and T. Katsuki, Tetrahedron Lett., 37, 9245 (1996). h) R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 32, 7373 (1991). i) D. Tanner, P. G. Anderson, A. Harden, and P. Somfai, Tetrahedron Lett., 35, 4631 (1994). j) A. M. Harm, J. G. Knight, and G. Stemp, Synlett, 1996, 677. k) T.-S. Lai, H.-L. Kwong, C.-M. Che, and S.-M. Peng, Chem. Commun., 1997, 2373. l) M. J. Södergren, D. A. Alonso, and P. G. Andersson, Tetrahedron: Asymmetry, 8, 3563 (1997). m) P. Müller, C. Baud, Y. Jacquier, M. Moran, and I. Nägeri, J. Phys. Org. Chem., 9, 341 (1996). R. S. Atkinson, W. T. Gattrell, A. P. Ayscough, and T. M. Raynham, Chem. Commun., 1996, 1935. Asymmetric aziridination usig chiral nitridomanganese complexes: o) S. Minakata, T. Ando, M. Nishimura, I. Ryu, and M. Komatsu, Chem. Commun., 1998, 3392. p) M. Nishimura, S. Minakata, T. Takahashi, Y. Oderaotoshi, and M. Komatsu, J. Org. Chem., 67, 2101 (2002).
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62
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- Asymmetric aziridination using PhI=NTs: a) D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991). b) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson, and D. M. Barnes, J. Am. Chem. Soc., 115, 5328 (1993). c) Z. Li, K. R. Conser, and E. N. Jacobsen, J. Am. Chem. Soc., 115, 5326 (1993). d) W. Zhang, N. H. Lee, and E. N. Jacobsen, J. Am. Chem. Soc., 116, 425 (1994). e) Z. Li, R. W. Quan, and E. N. Jacobsen, J. Am. Chem. Soc., 117, 5889 (1995). f) K. Noda, H. Hosoya, R. Irie, Y. Ito, and T. Katsuki, Synlett, 1993, 469. g) H. Nishikori and T. Katsuki, Tetrahedron Lett., 37, 9245 (1996). h) R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 32, 7373 (1991). i) D. Tanner, P. G. Anderson, A. Harden, and P. Somfai, Tetrahedron Lett., 35, 4631 (1994). j) A. M. Harm, J. G. Knight, and G. Stemp, Synlett, 1996, 677. k) T.-S. Lai, H.-L. Kwong, C.-M. Che, and S.-M. Peng, Chem. Commun., 1997, 2373. l) M. J. Södergren, D. A. Alonso, and P. G. Andersson, Tetrahedron: Asymmetry, 8, 3563 (1997). m) P. Müller, C. Baud, Y. Jacquier, M. Moran, and I. Nägeri, J. Phys. Org. Chem., 9, 341 (1996). R. S. Atkinson, W. T. Gattrell, A. P. Ayscough, and T. M. Raynham, Chem. Commun., 1996, 1935. Asymmetric aziridination usig chiral nitridomanganese complexes: o) S. Minakata, T. Ando, M. Nishimura, I. Ryu, and M. Komatsu, Chem. Commun., 1998, 3392. p) M. Nishimura, S. Minakata, T. Takahashi, Y. Oderaotoshi, and M. Komatsu, J. Org. Chem., 67, 2101 (2002).
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- Asymmetric aziridination using PhI=NTs: a) D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991). b) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson, and D. M. Barnes, J. Am. Chem. Soc., 115, 5328 (1993). c) Z. Li, K. R. Conser, and E. N. Jacobsen, J. Am. Chem. Soc., 115, 5326 (1993). d) W. Zhang, N. H. Lee, and E. N. Jacobsen, J. Am. Chem. Soc., 116, 425 (1994). e) Z. Li, R. W. Quan, and E. N. Jacobsen, J. Am. Chem. Soc., 117, 5889 (1995). f) K. Noda, H. Hosoya, R. Irie, Y. Ito, and T. Katsuki, Synlett, 1993, 469. g) H. Nishikori and T. Katsuki, Tetrahedron Lett., 37, 9245 (1996). h) R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 32, 7373 (1991). i) D. Tanner, P. G. Anderson, A. Harden, and P. Somfai, Tetrahedron Lett., 35, 4631 (1994). j) A. M. Harm, J. G. Knight, and G. Stemp, Synlett, 1996, 677. k) T.-S. Lai, H.-L. Kwong, C.-M. Che, and S.-M. Peng, Chem. Commun., 1997, 2373. l) M. J. Södergren, D. A. Alonso, and P. G. Andersson, Tetrahedron: Asymmetry, 8, 3563 (1997). m) P. Müller, C. Baud, Y. Jacquier, M. Moran, and I. Nägeri, J. Phys. Org. Chem., 9, 341 (1996). R. S. Atkinson, W. T. Gattrell, A. P. Ayscough, and T. M. Raynham, Chem. Commun., 1996, 1935. Asymmetric aziridination usig chiral nitridomanganese complexes: o) S. Minakata, T. Ando, M. Nishimura, I. Ryu, and M. Komatsu, Chem. Commun., 1998, 3392. p) M. Nishimura, S. Minakata, T. Takahashi, Y. Oderaotoshi, and M. Komatsu, J. Org. Chem., 67, 2101 (2002).
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64
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- Asymmetric aziridination using PhI=NTs: a) D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991). b) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson, and D. M. Barnes, J. Am. Chem. Soc., 115, 5328 (1993). c) Z. Li, K. R. Conser, and E. N. Jacobsen, J. Am. Chem. Soc., 115, 5326 (1993). d) W. Zhang, N. H. Lee, and E. N. Jacobsen, J. Am. Chem. Soc., 116, 425 (1994). e) Z. Li, R. W. Quan, and E. N. Jacobsen, J. Am. Chem. Soc., 117, 5889 (1995). f) K. Noda, H. Hosoya, R. Irie, Y. Ito, and T. Katsuki, Synlett, 1993, 469. g) H. Nishikori and T. Katsuki, Tetrahedron Lett., 37, 9245 (1996). h) R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 32, 7373 (1991). i) D. Tanner, P. G. Anderson, A. Harden, and P. Somfai, Tetrahedron Lett., 35, 4631 (1994). j) A. M. Harm, J. G. Knight, and G. Stemp, Synlett, 1996, 677. k) T.-S. Lai, H.-L. Kwong, C.-M. Che, and S.-M. Peng, Chem. Commun., 1997, 2373. l) M. J. Södergren, D. A. Alonso, and P. G. Andersson, Tetrahedron: Asymmetry, 8, 3563 (1997). m) P. Müller, C. Baud, Y. Jacquier, M. Moran, and I. Nägeri, J. Phys. Org. Chem., 9, 341 (1996). R. S. Atkinson, W. T. Gattrell, A. P. Ayscough, and T. M. Raynham, Chem. Commun., 1996, 1935. Asymmetric aziridination usig chiral nitridomanganese complexes: o) S. Minakata, T. Ando, M. Nishimura, I. Ryu, and M. Komatsu, Chem. Commun., 1998, 3392. p) M. Nishimura, S. Minakata, T. Takahashi, Y. Oderaotoshi, and M. Komatsu, J. Org. Chem., 67, 2101 (2002).
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- Asymmetric aziridination using PhI=NTs: a) D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991). b) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson, and D. M. Barnes, J. Am. Chem. Soc., 115, 5328 (1993). c) Z. Li, K. R. Conser, and E. N. Jacobsen, J. Am. Chem. Soc., 115, 5326 (1993). d) W. Zhang, N. H. Lee, and E. N. Jacobsen, J. Am. Chem. Soc., 116, 425 (1994). e) Z. Li, R. W. Quan, and E. N. Jacobsen, J. Am. Chem. Soc., 117, 5889 (1995). f) K. Noda, H. Hosoya, R. Irie, Y. Ito, and T. Katsuki, Synlett, 1993, 469. g) H. Nishikori and T. Katsuki, Tetrahedron Lett., 37, 9245 (1996). h) R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 32, 7373 (1991). i) D. Tanner, P. G. Anderson, A. Harden, and P. Somfai, Tetrahedron Lett., 35, 4631 (1994). j) A. M. Harm, J. G. Knight, and G. Stemp, Synlett, 1996, 677. k) T.-S. Lai, H.-L. Kwong, C.-M. Che, and S.-M. Peng, Chem. Commun., 1997, 2373. l) M. J. Södergren, D. A. Alonso, and P. G. Andersson, Tetrahedron: Asymmetry, 8, 3563 (1997). m) P. Müller, C. Baud, Y. Jacquier, M. Moran, and I. Nägeri, J. Phys. Org. Chem., 9, 341 (1996). R. S. Atkinson, W. T. Gattrell, A. P. Ayscough, and T. M. Raynham, Chem. Commun., 1996, 1935. Asymmetric aziridination usig chiral nitridomanganese complexes: o) S. Minakata, T. Ando, M. Nishimura, I. Ryu, and M. Komatsu, Chem. Commun., 1998, 3392. p) M. Nishimura, S. Minakata, T. Takahashi, Y. Oderaotoshi, and M. Komatsu, J. Org. Chem., 67, 2101 (2002).
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- Asymmetric aziridination using PhI=NTs: a) D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991). b) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson, and D. M. Barnes, J. Am. Chem. Soc., 115, 5328 (1993). c) Z. Li, K. R. Conser, and E. N. Jacobsen, J. Am. Chem. Soc., 115, 5326 (1993). d) W. Zhang, N. H. Lee, and E. N. Jacobsen, J. Am. Chem. Soc., 116, 425 (1994). e) Z. Li, R. W. Quan, and E. N. Jacobsen, J. Am. Chem. Soc., 117, 5889 (1995). f) K. Noda, H. Hosoya, R. Irie, Y. Ito, and T. Katsuki, Synlett, 1993, 469. g) H. Nishikori and T. Katsuki, Tetrahedron Lett., 37, 9245 (1996). h) R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 32, 7373 (1991). i) D. Tanner, P. G. Anderson, A. Harden, and P. Somfai, Tetrahedron Lett., 35, 4631 (1994). j) A. M. Harm, J. G. Knight, and G. Stemp, Synlett, 1996, 677. k) T.-S. Lai, H.-L. Kwong, C.-M. Che, and S.-M. Peng, Chem. Commun., 1997, 2373. l) M. J. Södergren, D. A. Alonso, and P. G. Andersson, Tetrahedron: Asymmetry, 8, 3563 (1997). m) P. Müller, C. Baud, Y. Jacquier, M. Moran, and I. Nägeri, J. Phys. Org. Chem., 9, 341 (1996). R. S. Atkinson, W. T. Gattrell, A. P. Ayscough, and T. M. Raynham, Chem. Commun., 1996, 1935. Asymmetric aziridination usig chiral nitridomanganese complexes: o) S. Minakata, T. Ando, M. Nishimura, I. Ryu, and M. Komatsu, Chem. Commun., 1998, 3392. p) M. Nishimura, S. Minakata, T. Takahashi, Y. Oderaotoshi, and M. Komatsu, J. Org. Chem., 67, 2101 (2002).
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95
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- 11b

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