메뉴 건너뛰기




Volumn 132, Issue 4, 2010, Pages 1255-1257

Catalytic asymmetric synthesis of 3-aminooxindoles: Enantiofacial selectivity switch in bimetallic vs monometallic schiff base catalysis

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUPS;

EID: 77950340760     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja908906n     Document Type: Article
Times cited : (253)

References (51)
  • 1
    • 0042379984 scopus 로고    scopus 로고
    • Reviews:(a) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
    • Reviews:(a) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
  • 3
    • 0034812533 scopus 로고    scopus 로고
    • 3-Aminooxindoles in medicinal chemistry: (a) Ochi, M.; Kawasaki, K.; Kataoka, H.; Uchio, Y. Biochem. Biophys. Res. Commun. 2001, 283, 1118.
    • 3-Aminooxindoles in medicinal chemistry: (a) Ochi, M.; Kawasaki, K.; Kataoka, H.; Uchio, Y. Biochem. Biophys. Res. Commun. 2001, 283, 1118.
  • 9
    • 33845919566 scopus 로고    scopus 로고
    • Hydroxylation of oxindoles: (a) Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S. J. Am. Chem. Soc. 2006, 128, 16488.
    • Hydroxylation of oxindoles: (a) Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S. J. Am. Chem. Soc. 2006, 128, 16488.
  • 10
    • 44449174208 scopus 로고    scopus 로고
    • 1593. Nucleophilic addition to isatins
    • (b) Sano, D.; Nagata, K.; Itoh, T. Org. Lett. 2008, 10, 1593. Nucleophilic addition to isatins:
    • (2008) Org. Lett , vol.10
    • Sano, D.1    Nagata, K.2    Itoh, T.3
  • 17
    • 69449106657 scopus 로고    scopus 로고
    • Itoh, T.; Ishikawa, H.; Hayashi, Y. Org. Lett. 2009, 11, 3854, and references therein. See also ref 6a.
    • (i) Itoh, T.; Ishikawa, H.; Hayashi, Y. Org. Lett. 2009, 11, 3854, and references therein. See also ref 6a.
  • 18
    • 33750492631 scopus 로고    scopus 로고
    • For diastereoselective approaches using chiral auxiliaries: a
    • For diastereoselective approaches using chiral auxiliaries: (a) Emura, T.; Esaki, T.; Tachibana, K.; Shimizu, M. J. Org. Chem. 2006, 71, 8559.
    • (2006) J. Org. Chem , vol.71 , pp. 8559
    • Emura, T.1    Esaki, T.2    Tachibana, K.3    Shimizu, M.4
  • 20
    • 50849107654 scopus 로고    scopus 로고
    • Jia, Y.-X.; Hillgren, J. M.; Watson, E. L.; Marsden, S. P.; Kündig, E. P. Chem Commun. 2008, 4040. For a different approach, see also:
    • (a) Jia, Y.-X.; Hillgren, J. M.; Watson, E. L.; Marsden, S. P.; Kündig, E. P. Chem Commun. 2008, 4040. For a different approach, see also:
  • 25
    • 69449091605 scopus 로고    scopus 로고
    • During review process, additional examples appeared
    • (a) Cheng, L.; Liu, L.; Wang, D.; Chen, Y.-J. Org. Lett. 2009, 11, 3874. During review process, additional examples appeared:
    • (2009) Org. Lett , vol.11 , pp. 3874
    • Cheng, L.1    Liu, L.2    Wang, D.3    Chen, Y.-J.4
  • 26
    • 70449371812 scopus 로고    scopus 로고
    • Qian, Z.-Q.; Zhou, F.; Du, T.-P.; Wang, B.-L.; Ding, M.; Zhao, X.-L.; Zhou, J. Chem. Commun. 2009, 6753. Barbas et al. successfully utilized 4a (one entry):
    • (b) Qian, Z.-Q.; Zhou, F.; Du, T.-P.; Wang, B.-L.; Ding, M.; Zhao, X.-L.; Zhou, J. Chem. Commun. 2009, 6753. Barbas et al. successfully utilized 4a (one entry):
  • 28
    • 33845477661 scopus 로고    scopus 로고
    • For the N-N bond cleavage of amination adducts from di-isopropyl azodicarboxylate, harsh reaction conditions, such as conc. HCl under reflux for 23 h, are required to remove isopropoxycarbonyl groups; see: Matsubara, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 7993.
    • For the N-N bond cleavage of amination adducts from di-isopropyl azodicarboxylate, harsh reaction conditions, such as conc. HCl under reflux for 23 h, are required to remove isopropoxycarbonyl groups; see: Matsubara, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 7993.
  • 29
    • 34247463317 scopus 로고    scopus 로고
    • Cu-Sm cat.: (a) Handa, S.; Gnanadesikan, V.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 4900. Pd-La cat.:
    • Cu-Sm cat.: (a) Handa, S.; Gnanadesikan, V.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 4900. Pd-La cat.:
  • 31
    • 39549091935 scopus 로고    scopus 로고
    • 2-1:
    • 2-1:
  • 35
    • 0037424485 scopus 로고    scopus 로고
    • For selected examples of related bifunctional bimetallic Schiff base complexes in asymmetric catalysis, see, a Annamalai, V, DiMauro, E. F, Carroll, P. J, Kozlowski, M. C. J. Org. Chem. 2003, 68, 1973, and references therein
    • For selected examples of related bifunctional bimetallic Schiff base complexes in asymmetric catalysis, see : (a) Annamalai, V.; DiMauro, E. F.; Carroll, P. J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 1973, and references therein.
  • 40
    • 84924257285 scopus 로고    scopus 로고
    • In our previous studies on direct Mannich-type reactions and Michael reactions using Ni2-1, Co2-1, and Mn 2-1 complexes, corresponding monometallic Ni, Co, and Mn-2a, 2b, and 2c complexes resulted in poor to modest reactivity and enantioselectivity. See ref 10c, 10d, and 11
    • 2-1 complexes, corresponding monometallic Ni-, Co-, and Mn-2a, 2b, and 2c complexes resulted in poor to modest reactivity and enantioselectivity. See ref 10c, 10d, and 11.
  • 41
    • 33744830047 scopus 로고    scopus 로고
    • Reversal of enantioselectivity depending on the number of assembled metals in multimetallic complexes; see:(a) Kato, N, Mita, T, Kanai, M, Therrien, B, Kawano, M, Yamaguchi, K, Danjo, H, Sei, Y, Sato, A, Furusho, S, Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6768
    • Reversal of enantioselectivity depending on the number of assembled metals in multimetallic complexes; see:(a) Kato, N.; Mita, T.; Kanai, M.; Therrien, B.; Kawano, M.; Yamaguchi, K.; Danjo, H.; Sei, Y.; Sato, A.; Furusho, S.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6768.
  • 42
    • 33845944635 scopus 로고    scopus 로고
    • For selected leading examples on metal-dependent reversal of enantioselectivity with >90% ee, see
    • (b) Fujimori, I.; Mita, T.; Maki, K.; Shiro, M.; Sato, A.; Furusho, S.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 16438. For selected leading examples on metal-dependent reversal of enantioselectivity with >90% ee, see:
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 16438
    • Fujimori, I.1    Mita, T.2    Maki, K.3    Shiro, M.4    Sato, A.5    Furusho, S.6    Kanai, M.7    Shibasaki, M.8
  • 46
    • 84924237173 scopus 로고    scopus 로고
    • N-H free oxindole resulted in <10% ee. 3-Ph-substituted oxindole gave product in 94% yield but in only 30% ee. Studies to improve substrate generality are ongoing.
    • N-H free oxindole resulted in <10% ee. 3-Ph-substituted oxindole gave product in 94% yield but in only 30% ee. Studies to improve substrate generality are ongoing.
  • 47
    • 33645783386 scopus 로고    scopus 로고
    • Synthetic studies through 3-aminooxindoles with a spiro-β-lactam unit: (a) Sun, C.; Lin, X.; Weinreb, S. M. J. Org. Chem. 2006, 71, 3159.
    • Synthetic studies through 3-aminooxindoles with a spiro-β-lactam unit: (a) Sun, C.; Lin, X.; Weinreb, S. M. J. Org. Chem. 2006, 71, 3159.
  • 49
    • 3142678923 scopus 로고    scopus 로고
    • Nishikawa, T.; Kajii, S.; Isobe, M. Chem. Lett. 2004, 33, 440. See also ref 6b and references therein.
    • (c) Nishikawa, T.; Kajii, S.; Isobe, M. Chem. Lett. 2004, 33, 440. See also ref 6b and references therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.