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Volumn 129, Issue 31, 2007, Pages 9588-9589

Lanthanum aryloxide/pybox-catalyzed direct asymmetric mannich-type reactions using a trichloromethyl ketone as a propionate equivalent donor

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; LANTHANUM; OXIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPIONIC ACID; TRICHLOROMETHYL KETONE; UNCLASSIFIED DRUG;

EID: 34547803869     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073285p     Document Type: Article
Times cited : (110)

References (37)
  • 4
    • 33644937519 scopus 로고    scopus 로고
    • Selected recent direct Mannich-type reactions of ketones and aldehydes: (a) Trost, B. M.; Jaratjaroonphong, J.; Reutrakul, V. J. Am. Chem. Soc. 2006, 128, 2778.
    • Selected recent direct Mannich-type reactions of ketones and aldehydes: (a) Trost, B. M.; Jaratjaroonphong, J.; Reutrakul, V. J. Am. Chem. Soc. 2006, 128, 2778.
  • 9
    • 0038298158 scopus 로고    scopus 로고
    • Direct aldol reactions using ester equivalent donors: (a) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706.
    • Direct aldol reactions using ester equivalent donors: (a) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706.
  • 13
    • 22744453251 scopus 로고    scopus 로고
    • (α-Hydroxyacetyl)pyrrole as a donor: Harada, S.; Handa, S.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2005, 44, 4365.
    • (α-Hydroxyacetyl)pyrrole as a donor: Harada, S.; Handa, S.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2005, 44, 4365.
  • 19
    • 0037419152 scopus 로고    scopus 로고
    • With glycine Schiff base: (f) Bernardi, L, Gothelf, A. S, Hazell, R. G, Jørgensen, K. A. J. Org. Chem. 2003, 68, 2583
    • With glycine Schiff base: (f) Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 2583.
  • 25
    • 84989540865 scopus 로고    scopus 로고
    • Utility of trichloromethyl ketones and trichloromethyl carbinols as building blocks: (a) Corey, E. J.; Link, J. O. J. Am. Chem. Soc. 1992, 114, 1906.
    • Utility of trichloromethyl ketones and trichloromethyl carbinols as building blocks: (a) Corey, E. J.; Link, J. O. J. Am. Chem. Soc. 1992, 114, 1906.
  • 26
    • 0026751962 scopus 로고    scopus 로고
    • Corey, E. J.; Link, J. O. Tetrahedron Lett. 1992, 33, 3431. See also ref 6 and references therein.
    • (b) Corey, E. J.; Link, J. O. Tetrahedron Lett. 1992, 33, 3431. See also ref 6 and references therein.
  • 29
    • 34547798228 scopus 로고    scopus 로고
    • N-Heteroarenesulfonyl imines showed better enantioselectivity than other imines such as N-Ts imines and N-diphenylphosphinoyl imines. For selected recent examples of N-heteroarenesulfonyl imines in asymmetric synthesis: (a) González, A. S.; Gómez Arrayás, R.; Carretero, J. C. Org. Lett. 2006, 8, 2977 and references therein.
    • N-Heteroarenesulfonyl imines showed better enantioselectivity than other imines such as N-Ts imines and N-diphenylphosphinoyl imines. For selected recent examples of N-heteroarenesulfonyl imines in asymmetric synthesis: (a) González, A. S.; Gómez Arrayás, R.; Carretero, J. C. Org. Lett. 2006, 8, 2977 and references therein.
  • 30
    • 33846999920 scopus 로고    scopus 로고
    • Esquivias, J.; Gómez, Arrayás, R.; Carretero, J. C. J. Am. Chem. Soc. 2007, 129, 1480.
    • (b) Esquivias, J.; Gómez, Arrayás, R.; Carretero, J. C. J. Am. Chem. Soc. 2007, 129, 1480.
  • 32
    • 0043240876 scopus 로고    scopus 로고
    • For utility of rare earth metal (RE) triflate and/or halide-pybox complexes as chiral Lewis acids, see a review: (a) Desimoni, G.; Faita, G.; Quadrelli, P. Chem. Rev. 2003, 103, 3119.
    • For utility of rare earth metal (RE) triflate and/or halide-pybox complexes as chiral Lewis acids, see a review: (a) Desimoni, G.; Faita, G.; Quadrelli, P. Chem. Rev. 2003, 103, 3119.
  • 34
    • 0034611489 scopus 로고    scopus 로고
    • 3/pybox complex as a bifunctional catalyst to generate nucleophilic RE-cyanide species, see: (c) Schaus, S. E.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001.
    • 3/pybox complex as a bifunctional catalyst to generate nucleophilic RE-cyanide species, see: (c) Schaus, S. E.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001.
  • 36
    • 34547815362 scopus 로고    scopus 로고
    • 3/pybox to form more basic ate complex or (b) LiOAr deprotonates 1 to form Li-enolate, followed by rapid transmetallation to generate La-enolate. Further mechanistic studies to clarify the role of LiOAr are ongoing.
    • 3/pybox to form more basic ate complex or (b) LiOAr deprotonates 1 to form Li-enolate, followed by rapid transmetallation to generate La-enolate. Further mechanistic studies to clarify the role of LiOAr are ongoing.
  • 37
    • 34547745670 scopus 로고    scopus 로고
    • 2Ph in Figure 1) gave Mannich adduct from imine 1b in 94% yield, syn/anti = 7.4:1, and 78% ee after 20 h. Further optimization studies using 1b and 1c are ongoing.
    • 2Ph in Figure 1) gave Mannich adduct from imine 1b in 94% yield, syn/anti = 7.4:1, and 78% ee after 20 h. Further optimization studies using 1b and 1c are ongoing.


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