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Volumn 130, Issue 40, 2008, Pages 13321-13332

Development of catalytic asymmetric 1,4-addition and [3 + 2] cycloaddition reactions using chiral calcium complexes

Author keywords

[No Author keywords available]

Indexed keywords

ABS RESINS; CALCIUM; CALCIUM ALLOYS; CHEMICAL REACTIONS; CYCLOADDITION; DYES; ENANTIOSELECTIVITY; ESTERS; LIGANDS; NUCLEAR MAGNETIC RESONANCE; NUCLEIC ACIDS; ORGANIC COMPOUNDS; ORGANIC POLYMERS; RNA; SPECTROSCOPIC ANALYSIS;

EID: 53549124720     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8032058     Document Type: Article
Times cited : (204)

References (116)
  • 1
    • 0004076526 scopus 로고
    • 3rd ed, Cotton, F. A, Wilkinson, G, Gaus, P. L, Eds, Wiley: New York
    • Basic Inorganic Chemistry, 3rd ed.; Cotton, F. A., Wilkinson, G., Gaus, P. L., Eds.; Wiley: New York, 1995.
    • (1995) Basic Inorganic Chemistry
  • 7
    • 0004005454 scopus 로고
    • Atkinson, R. S, Ed, Wiley-VCH: Chichester, U.K
    • (b) Stereoselective Synthesis; Atkinson, R. S., Ed.; Wiley-VCH: Chichester, U.K., 1995.
    • (1995) Stereoselective Synthesis
  • 8
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Heidelberg, Germany
    • (a) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, Germany, 1999.
    • (1999) Comprehensive Asymmetric Catalysis
  • 9
    • 0003544583 scopus 로고    scopus 로고
    • 2nd ed, Ojima, I, Ed, Wiley-VCH: New York
    • (b) Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
    • (2000) Catalytic Asymmetric Synthesis
  • 10
  • 16
    • 39749156976 scopus 로고    scopus 로고
    • For use of the Sr catalyst see
    • (e) For use of the Sr catalyst see: Agostinho, M.; Kobayashi, S. J. Am. Chem. Soc. 2008, 130, 2430.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 2430
    • Agostinho, M.1    Kobayashi, S.2
  • 17
    • 33749828310 scopus 로고    scopus 로고
    • Asymmetric reactions using the Box ligand: Desimoni, G.; Faita, G.; Jørgensen, K. A. Chem. Rev. 2006, 106, 3561.
    • Asymmetric reactions using the Box ligand: Desimoni, G.; Faita, G.; Jørgensen, K. A. Chem. Rev. 2006, 106, 3561.
  • 32
    • 0042880949 scopus 로고    scopus 로고
    • Synthesis of α-amino acid derivatives: (a) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
    • Synthesis of α-amino acid derivatives: (a) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
  • 51
    • 53549118225 scopus 로고    scopus 로고
    • Stereoselective synthesis of 4-substituted glutamic acid derivatives: Belokon, Y. N.; et al. J. Am. Chem. Soc. 2003, 125, 12860.
    • Stereoselective synthesis of 4-substituted glutamic acid derivatives: Belokon, Y. N.; et al. J. Am. Chem. Soc. 2003, 125, 12860.
  • 52
    • 58149271695 scopus 로고    scopus 로고
    • Stereoselective synthesis of 3-substituted glutamic acid derivatives: Soloshonok, V. A
    • (a) Stereoselective synthesis of 3-substituted glutamic acid derivatives: Soloshonok, V. A. Curr. Org. Chem. 2002, 6, 341.
    • (2002) Curr. Org. Chem , vol.6 , pp. 341
  • 53
    • 33845558580 scopus 로고    scopus 로고
    • Other representative examples: (b) Mauger, A. B. J. Org. Chem. 1981, 46, 1032.
    • Other representative examples: (b) Mauger, A. B. J. Org. Chem. 1981, 46, 1032.
  • 63
    • 53549105192 scopus 로고    scopus 로고
    • For some recent reviews and examples on catalytic asymmetric [3 + 2] cycloaddion reactions see: (a) Padwa, A.; Pearson, W. H. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; John Wiley & Sons: New York, 2002.
    • For some recent reviews and examples on catalytic asymmetric [3 + 2] cycloaddion reactions see: (a) Padwa, A.; Pearson, W. H. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; John Wiley & Sons: New York, 2002.
  • 74
    • 0041931082 scopus 로고    scopus 로고
    • Syntheses of quaternary carbon centers in asymmetric [3 + 2] cycloaddition reactions: (l) Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174.
    • Syntheses of quaternary carbon centers in asymmetric [3 + 2] cycloaddition reactions: (l) Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174.
  • 80
    • 20644453128 scopus 로고    scopus 로고
    • Intramolecular symmetric [3 + 2] cycloadditon reaction: (r) Stohler, R.; Wahl, F.; Pfaltz, A. Synthesis 2005, 1431.
    • Intramolecular symmetric [3 + 2] cycloadditon reaction: (r) Stohler, R.; Wahl, F.; Pfaltz, A. Synthesis 2005, 1431.
  • 81
    • 34447315556 scopus 로고    scopus 로고
    • Organocatalytic asymmetric [3 + 2] cycloaddition reactions: (s) Vicario, J. L.; Reboredo, S.; Badía, D.; Carrillo, L. Angew. Chem., Int. Ed. 2007, 46, 5168.
    • Organocatalytic asymmetric [3 + 2] cycloaddition reactions: (s) Vicario, J. L.; Reboredo, S.; Badía, D.; Carrillo, L. Angew. Chem., Int. Ed. 2007, 46, 5168.
  • 83
    • 53549083464 scopus 로고    scopus 로고
    • For an example of a [3, 2] cycloadditon reaction using N-diphenylmethylene-protected glycine, see ref 17m, o
    • For an example of a [3 + 2] cycloadditon reaction using N-diphenylmethylene-protected glycine, see ref 17m, o.
  • 84
    • 53549130190 scopus 로고    scopus 로고
    • For an example of a [3, 2] cycloaddition reaction using crotonate. see ref 171
    • For an example of a [3 + 2] cycloaddition reaction using crotonate. see ref 171.
  • 85
    • 53549133886 scopus 로고    scopus 로고
    • Syntheses of contiguous chiral tertiary and quaternary carbon ceters using β-substituted acrylates were not reported, but those using maleimides were reported; see ref 17m,o,p
    • Syntheses of contiguous chiral tertiary and quaternary carbon ceters using β-substituted acrylates were not reported, but those using maleimides were reported; see ref 17m,o,p.
  • 91
    • 0000545418 scopus 로고
    • 5th ed, Wolff, M. E, Ed, John Wiley & Sons: New York, Chapter 20, pp
    • Goodman, M.; Ro, S. In Burger's Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1, Chapter 20, pp 803-861.
    • (1995) Burger's Medicinal Chemistry and Drug Discovery , vol.1 , pp. 803-861
    • Goodman, M.1    Ro, S.2
  • 92
    • 33750014969 scopus 로고    scopus 로고
    • Asymmetric alkylation of a cysteine Schiff base has been reported: (a) Kim, T.-S.; Lee, Y.-J.; Jeong, B.-S.; Park, H.-g.; Jew, S.-s. J. Org. Chem. 2006, 71, 8276.
    • Asymmetric alkylation of a cysteine Schiff base has been reported: (a) Kim, T.-S.; Lee, Y.-J.; Jeong, B.-S.; Park, H.-g.; Jew, S.-s. J. Org. Chem. 2006, 71, 8276.
  • 93
    • 3242877414 scopus 로고    scopus 로고
    • Other related works: (b) Jew, S.-s.; Lee, Y.-J.; Lee, J.; Kang, M. J.; Jeong, B.-S.; Lee, J.-H.; Yoo, M.-S.; Kim, M.-J.; Choi, S.-h.; Ku, J.-M.; Park, H.-g. Angew. Chem., Int. Ed. 2004, 43, 2382.
    • Other related works: (b) Jew, S.-s.; Lee, Y.-J.; Lee, J.; Kang, M. J.; Jeong, B.-S.; Lee, J.-H.; Yoo, M.-S.; Kim, M.-J.; Choi, S.-h.; Ku, J.-M.; Park, H.-g. Angew. Chem., Int. Ed. 2004, 43, 2382.
  • 103
    • 53549124897 scopus 로고    scopus 로고
    • We could not exclude a possibility that the complexes formed in the catalyst solution were a Ca-ligand (1:2) complex; however, real active species should be a Ca-ligand (1:1) complex
    • (h) We could not exclude a possibility that the complexes formed in the catalyst solution were a Ca-ligand (1:2) complex; however, real active species should be a Ca-ligand (1:1) complex.


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