메뉴 건너뛰기




Volumn 23, Issue 10, 2004, Pages 2238-2250

IAN amines: Chiral C 2-symmetric zirconium(IV) complexes from readily modified axially chiral C 1-symmetric β-diketimines

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXES; DIASTEREOSELECTIVITY; LIGANDS; TRANSAMINATION;

EID: 2542517672     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049897p     Document Type: Article
Times cited : (39)

References (99)
  • 7
    • 0000868533 scopus 로고
    • Selected examples of well-characterized systems: (a) Halpern, J. Science 1982, 217, 401. (b) Norrby, P.-O.; Becker, H.; Sharpless, K. B. J. Am. Chem. Soc. 1996, 118, 35.
    • (1982) Science , vol.217 , pp. 401
    • Halpern, J.1
  • 9
    • 29344449167 scopus 로고    scopus 로고
    • Review: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2923. (b) Kagan, H. B. Synlett 2001, 888. (c) Kagan, H. B.; Luukas, T. O. In Comprehensive Asymmetric Catalysis I-III; Springer: New York, 1999; Vol. 1, pp 101-118. Selected recent examples: (d) Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem. Eur. J. 2002, 8, 5211. (e) Buono, F.; Walsh, P. J.; Blackmond, D. G. J. Am. Chem. Soc. 2002, 124, 13652. (f) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10836.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 2923
    • Girard, C.1    Kagan, H.B.2
  • 10
    • 0034977429 scopus 로고    scopus 로고
    • Review: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2923. (b) Kagan, H. B. Synlett 2001, 888. (c) Kagan, H. B.; Luukas, T. O. In Comprehensive Asymmetric Catalysis I-III; Springer: New York, 1999; Vol. 1, pp 101-118. Selected recent examples: (d) Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem. Eur. J. 2002, 8, 5211. (e) Buono, F.; Walsh, P. J.; Blackmond, D. G. J. Am. Chem. Soc. 2002, 124, 13652. (f) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10836.
    • (2001) Synlett , pp. 888
    • Kagan, H.B.1
  • 11
    • 0000906552 scopus 로고    scopus 로고
    • Springer: New York
    • Review: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2923. (b) Kagan, H. B. Synlett 2001, 888. (c) Kagan, H. B.; Luukas, T. O. In Comprehensive Asymmetric Catalysis I-III; Springer: New York, 1999; Vol. 1, pp 101-118. Selected recent examples: (d) Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem. Eur. J. 2002, 8, 5211. (e) Buono, F.; Walsh, P. J.; Blackmond, D. G. J. Am. Chem. Soc. 2002, 124, 13652. (f) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10836.
    • (1999) Comprehensive Asymmetric Catalysis I-III , vol.1 , pp. 101-118
    • Kagan, H.B.1    Luukas, T.O.2
  • 12
    • 2242495403 scopus 로고    scopus 로고
    • Review: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2923. (b) Kagan, H. B. Synlett 2001, 888. (c) Kagan, H. B.; Luukas, T. O. In Comprehensive Asymmetric Catalysis I-III; Springer: New York, 1999; Vol. 1, pp 101-118. Selected recent examples: (d) Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem. Eur. J. 2002, 8, 5211. (e) Buono, F.; Walsh, P. J.; Blackmond, D. G. J. Am. Chem. Soc. 2002, 124, 13652. (f) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10836.
    • (2002) Chem. Eur. J. , vol.8 , pp. 5211
    • Steigelmann, M.1    Nisar, Y.2    Rominger, F.3    Goldfuss, B.4
  • 13
    • 0037145992 scopus 로고    scopus 로고
    • Review: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2923. (b) Kagan, H. B. Synlett 2001, 888. (c) Kagan, H. B.; Luukas, T. O. In Comprehensive Asymmetric Catalysis I-III; Springer: New York, 1999; Vol. 1, pp 101-118. Selected recent examples: (d) Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem. Eur. J. 2002, 8, 5211. (e) Buono, F.; Walsh, P. J.; Blackmond, D. G. J. Am. Chem. Soc. 2002, 124, 13652. (f) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10836.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 13652
    • Buono, F.1    Walsh, P.J.2    Blackmond, D.G.3
  • 14
    • 0037019652 scopus 로고    scopus 로고
    • Review: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2923. (b) Kagan, H. B. Synlett 2001, 888. (c) Kagan, H. B.; Luukas, T. O. In Comprehensive Asymmetric Catalysis I-III; Springer: New York, 1999; Vol. 1, pp 101-118. Selected recent examples: (d) Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem. Eur. J. 2002, 8, 5211. (e) Buono, F.; Walsh, P. J.; Blackmond, D. G. J. Am. Chem. Soc. 2002, 124, 13652. (f) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10836.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10836
    • Balsells, J.1    Davis, T.J.2    Carroll, P.3    Walsh, P.J.4
  • 16
    • 0000251826 scopus 로고    scopus 로고
    • For example: (a) Shibasaki, M.; Sasai, H. Top. Stereochem. 1999, 22, 201-225. (b) Shibasaki, M.; Sasai, H. Adv. Asymmetric Synth. 1998, 3, 191-233.
    • (1999) Top. Stereochem. , vol.22 , pp. 201-225
    • Shibasaki, M.1    Sasai, H.2
  • 17
    • 0000251826 scopus 로고    scopus 로고
    • For example: (a) Shibasaki, M.; Sasai, H. Top. Stereochem. 1999, 22, 201-225. (b) Shibasaki, M.; Sasai, H. Adv. Asymmetric Synth. 1998, 3, 191-233.
    • (1998) Adv. Asymmetric Synth. , vol.3 , pp. 191-233
    • Shibasaki, M.1    Sasai, H.2
  • 19
    • 0033714636 scopus 로고    scopus 로고
    • For reviews on nitrogen-containing ligands for asymmetric catalysis, see: (a) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159. (b) McCarthy, M.; Guiry, P. J. Tetrahedron 2001, 57, 3809.
    • (2000) Chem. Rev. , vol.100 , pp. 2159
    • Fache, F.1    Schulz, E.2    Tommasino, M.L.3    Lemaire, M.4
  • 20
    • 0035971715 scopus 로고    scopus 로고
    • For reviews on nitrogen-containing ligands for asymmetric catalysis, see: (a) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159. (b) McCarthy, M.; Guiry, P. J. Tetrahedron 2001, 57, 3809.
    • (2001) Tetrahedron , vol.57 , pp. 3809
    • McCarthy, M.1    Guiry, P.J.2
  • 24
    • 0035953024 scopus 로고    scopus 로고
    • For other derivatives within this class not shown, see: (a) Tucker, S. C.; Brown, J.; Oakes, J.; Thornthwaite, D. Tetrahedron 2001, 57, 2545. (b) Brunner, H.; Olschewski, G.; Nuber, B. Synthesis 1999, 3, 429. (c) Tsue, H.; Fujinami, H.; Itakura, T.; Tsuchiya, R.; Kobayashi, K.; Takahashi, H.; Hirao, K. J. Chem. Soc., Perkin Trans. 1 1998, 3677. (d) Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879.
    • (2001) Tetrahedron , vol.57 , pp. 2545
    • Tucker, S.C.1    Brown, J.2    Oakes, J.3    Thornthwaite, D.4
  • 25
    • 0033064421 scopus 로고    scopus 로고
    • For other derivatives within this class not shown, see: (a) Tucker, S. C.; Brown, J.; Oakes, J.; Thornthwaite, D. Tetrahedron 2001, 57, 2545. (b) Brunner, H.; Olschewski, G.; Nuber, B. Synthesis 1999, 3, 429. (c) Tsue, H.; Fujinami, H.; Itakura, T.; Tsuchiya, R.; Kobayashi, K.; Takahashi, H.; Hirao, K. J. Chem. Soc., Perkin Trans. 1 1998, 3677. (d) Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879.
    • (1999) Synthesis , vol.3 , pp. 429
    • Brunner, H.1    Olschewski, G.2    Nuber, B.3
  • 26
    • 0003088057 scopus 로고    scopus 로고
    • For other derivatives within this class not shown, see: (a) Tucker, S. C.; Brown, J.; Oakes, J.; Thornthwaite, D. Tetrahedron 2001, 57, 2545. (b) Brunner, H.; Olschewski, G.; Nuber, B. Synthesis 1999, 3, 429. (c) Tsue, H.; Fujinami, H.; Itakura, T.; Tsuchiya, R.; Kobayashi, K.; Takahashi, H.; Hirao, K. J. Chem. Soc., Perkin Trans. 1 1998, 3677. (d) Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 3677
    • Tsue, H.1    Fujinami, H.2    Itakura, T.3    Tsuchiya, R.4    Kobayashi, K.5    Takahashi, H.6    Hirao, K.7
  • 27
    • 0001408378 scopus 로고
    • For other derivatives within this class not shown, see: (a) Tucker, S. C.; Brown, J.; Oakes, J.; Thornthwaite, D. Tetrahedron 2001, 57, 2545. (b) Brunner, H.; Olschewski, G.; Nuber, B. Synthesis 1999, 3, 429. (c) Tsue, H.; Fujinami, H.; Itakura, T.; Tsuchiya, R.; Kobayashi, K.; Takahashi, H.; Hirao, K. J. Chem. Soc., Perkin Trans. 1 1998, 3677. (d) Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 879
    • Meyers, A.I.1    Lutomski, K.A.2
  • 39
    • 0036838404 scopus 로고    scopus 로고
    • Reviews: (a) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. Engl. 1999, 38, 428. (b) With Group 3 metals: Piers, W. E.; Emslie, D. J. H. Coord. Chem. Rev. 2002, 233, 131.
    • (2002) Coord. Chem. Rev. , vol.233 , pp. 131
    • Piers, W.E.1    Emslie, D.J.H.2
  • 40
    • 0036570894 scopus 로고    scopus 로고
    • For the use of a planar chiral (neutral) β-diketimine in the enantioselective copper(I)- catalyzed alkyne/nitrone coupling, see: Lo, M.-C. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4572
    • Lo, M.-C.L.1    Fu, G.C.2
  • 56
    • 2542643366 scopus 로고    scopus 로고
    • In accord with typical safe laboratory practice, the most recent toxicological data should be sought when preparing any organic compound. Although 2-aminonaphthalene is commercially labeled as a mutagen and should be handled appropriately, N-phenyl-2-naphthylamine was not found to be mutagenic in the Ames test: Kubo, T.; Urano, K.; Utsumi, H. J. Health Sci. 2002, 48, 545.
    • (2002) J. Health Sci. , vol.48 , pp. 545
    • Kubo, T.1    Urano, K.2    Utsumi, H.3
  • 61
    • 2542540032 scopus 로고    scopus 로고
    • note
    • In this and all subsequent crystal structures, the asymmetric unit cell is always paired with its mirror image. That is, the single crystals are (presumably) optically inactive.
  • 64
    • 2542611651 scopus 로고    scopus 로고
    • note
    • Zirconium amido complexes 14-18 immediately decompose to free ligand (1) upon contact with water.
  • 68
    • 2542579637 scopus 로고
    • Wiley: New York. Unpublished results of W. P. Jencks
    • a, values for pyridinium tosylate and dimethylanilinium tosylate are 5.21 and 5.20, respectively. March, J. Advanced Organic Chemistry, 3rd. ed.; Wiley: New York, 1985. Unpublished results of W. P. Jencks.
    • (1985) J. Advanced Organic Chemistry, 3rd. Ed.
  • 79
    • 0025752969 scopus 로고
    • The axially chiral bis(dimethylamino) binaphthylene derivative reported by Salvadori catalyzes the diethyl zinc addition in up to 64% ee: Rosini, C.; Franzini, L.; Iuliano, A.; Fini, D.; Salvadori, P. Tetrahedron: Asymmetry 1991, 2, 363. Reviews: (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (c) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 363
    • Rosini, C.1    Franzini, L.2    Iuliano, A.3    Fini, D.4    Salvadori, P.5
  • 80
    • 0035263817 scopus 로고    scopus 로고
    • The axially chiral bis(dimethylamino) binaphthylene derivative reported by Salvadori catalyzes the diethyl zinc addition in up to 64% ee: Rosini, C.; Franzini, L.; Iuliano, A.; Fini, D.; Salvadori, P. Tetrahedron: Asymmetry 1991, 2, 363. Reviews: (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (c) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
    • (2001) Chem. Rev. , vol.101 , pp. 757
    • Pu, L.1    Yu, H.-B.2
  • 81
    • 4244117250 scopus 로고
    • The axially chiral bis(dimethylamino) binaphthylene derivative reported by Salvadori catalyzes the diethyl zinc addition in up to 64% ee: Rosini, C.; Franzini, L.; Iuliano, A.; Fini, D.; Salvadori, P. Tetrahedron: Asymmetry 1991, 2, 363. Reviews: (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (c) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
    • (1992) Chem. Rev. , vol.92 , pp. 833
    • Soai, K.1    Niwa, S.2
  • 82
    • 33748247006 scopus 로고
    • The axially chiral bis(dimethylamino) binaphthylene derivative reported by Salvadori catalyzes the diethyl zinc addition in up to 64% ee: Rosini, C.; Franzini, L.; Iuliano, A.; Fini, D.; Salvadori, P. Tetrahedron: Asymmetry 1991, 2, 363. Reviews: (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (c) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 49
    • Noyori, R.1    Kitamura, M.2
  • 85
    • 0000250409 scopus 로고    scopus 로고
    • An example of a zirconium complex with amine, amido, and chloro ligands has been reported for olefin polymerization: Fuhrmann, H.; Brenner, S.; Arndt, P.; Kempe, R. Inorg. Chem. 1996, 35, 6742.
    • (1996) Inorg. Chem. , vol.35 , pp. 6742
    • Fuhrmann, H.1    Brenner, S.2    Arndt, P.3    Kempe, R.4
  • 96
    • 2542511020 scopus 로고    scopus 로고
    • note
    • Complete experimental details can be found in the Supporting Information.
  • 97
    • 0009575090 scopus 로고    scopus 로고
    • Bruker Analytical X-Ray Systems: Madison, WI
    • SAINT 6.1; Bruker Analytical X-Ray Systems: Madison, WI.
    • SAINT 6.1
  • 98
    • 0004150157 scopus 로고    scopus 로고
    • Bruker Analytical X-Ray Systems: Madison, WI
    • SHELXTL-Plus V 5.10; Bruker Analytical X-Ray Systems: Madison, WI.
    • SHELXTL-plus V 5.10
  • 99
    • 0004271269 scopus 로고    scopus 로고
    • Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations; Oak Ridge National Laboratory Report ORNL-6895
    • Burnett, M. N.; Johnson, C. K. ORTEP-III, Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations; Oak Ridge National Laboratory Report ORNL-6895, 1996.
    • (1996) ORTEP-III
    • Burnett, M.N.1    Johnson, C.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.