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MeSH Review

Cinchona

 
 
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Disease relevance of Cinchona

 

High impact information on Cinchona

  • The Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids: Enantioselective Synthesis of beta-Amino Acids [3].
  • Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids [4].
  • Cinchona alkaloid/sulfinyl chloride combinations: enantioselective sulfinylating agents of alcohols [5].
  • Chiral cinchona alkaloid derivatives work best when paired with Lewis acids based on Al(III), Zn(II), Sc(III), and, most notably, In(III) [6].
  • Origins of enantioselectivity in reductions of ketones on cinchona alkaloid modified platinum [7].
 

Biological context of Cinchona

 

Anatomical context of Cinchona

 

Associations of Cinchona with chemical compounds

  • Optically active (S)-alpha-amino acids are prepared in 54-95% ee (12 cases) by reaction of the Schiff base acetate of glycine tert-butyl ester with B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine, and base [11].
  • The zwitterionic adduct between a cinchona alkaloid and ketone is adsorbed on Pt through the quinoline ring and two heteroatoms and is subsequently reduced with inversion [7].
  • Elucidation of the chiral recognition mechanism of cinchona alkaloid carbamate-type receptors for 3,5-dinitrobenzoyl amino acids [12].
  • Highly enantioselective conjugate addition of malonate and beta-ketoester to nitroalkenes: asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids [13].
  • Asymmetric synthesis of alpha-amino acids via cinchona alkaloid-catalyzed kinetic resolution of urethane-protected alpha-amino acid N-carboxyanhydrides [14].
 

Gene context of Cinchona

  • The Cinchona alkaloid derived chiral ammonium salt developed by Park and Jew functions as an effective catalyst for the synthesis of beta-hydroxy alpha-amino acids via asymmetric aldol reactions under homogeneous conditions [15].
  • [reaction: see text] Acid chlorides and aromatic aldehydes react in the presence of a stoichiometric amount of a tertiary amine and catalytic amounts of a cinchona alkaloid derivative and a Lewis acid to produce beta-lactones in high diastereo- and enantioselectivity [16].
  • Optosensor for cinchona alkaloids with C18 silica gel as a substrate [17].
  • Direct STM investigation of cinchona alkaloid adsorption on Cu(III) [18].
  • Heterogeneous asymmetric reactions. Part 24. Heterogeneous catalytic enantioselective hydrogenation of the C==N group over cinchona alkaloid modified palladium catalyst [9].

References

  1. Treatment of malaria--1990. Panisko, D.M., Keystone, J.S. Drugs (1990) [Pubmed]
  2. Drug-specific characteristics of thrombocytopenia caused by non-cytotoxic drugs. Pedersen-Bjergaard, U., Andersen, M., Hansen, P.B. Eur. J. Clin. Pharmacol. (1998) [Pubmed]
  3. The Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids: Enantioselective Synthesis of beta-Amino Acids. Song, J., Wang, Y., Deng, L. J. Am. Chem. Soc. (2006) [Pubmed]
  4. Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids. Lou, S., Taoka, B.M., Ting, A., Schaus, S.E. J. Am. Chem. Soc. (2005) [Pubmed]
  5. Cinchona alkaloid/sulfinyl chloride combinations: enantioselective sulfinylating agents of alcohols. Shibata, N., Matsunaga, M., Nakagawa, M., Fukuzumi, T., Nakamura, S., Toru, T. J. Am. Chem. Soc. (2005) [Pubmed]
  6. Bifunctional Lewis acid-nucleophile-based asymmetric catalysis: mechanistic evidence for imine activation working in tandem with chiral enolate formation in the synthesis of beta-lactams. France, S., Shah, M.H., Weatherwax, A., Wack, H., Roth, J.P., Lectka, T. J. Am. Chem. Soc. (2005) [Pubmed]
  7. Origins of enantioselectivity in reductions of ketones on cinchona alkaloid modified platinum. Vayner, G., Houk, K.N., Sun, Y.K. J. Am. Chem. Soc. (2004) [Pubmed]
  8. Highly enantioselective amination of alpha-substituted alpha-cyanoacetates with chiral catalysts accessible from both quinine and quinidine. Liu, X., Li, H., Deng, L. Org. Lett. (2005) [Pubmed]
  9. Heterogeneous asymmetric reactions. Part 24. Heterogeneous catalytic enantioselective hydrogenation of the C==N group over cinchona alkaloid modified palladium catalyst. Szöllösi, G., Kun, I., Bartók, M. Chirality. (2001) [Pubmed]
  10. Biotransformation of n-hexadecane by cell suspension cultures of Cinchona robusta and Dioscorea composita. Vega-Jarquin, C., Dendooven, L., Magaña-Plaza, I., Thalasso, F., Ramos-Valdivia, A. Environ. Toxicol. Chem. (2001) [Pubmed]
  11. The enantioselective synthesis of alpha-amino acid derivatives via organoboranes. O'Donnell, M.J., Drew, M.D., Cooper, J.T., Delgado, F., Zhou, C. J. Am. Chem. Soc. (2002) [Pubmed]
  12. Elucidation of the chiral recognition mechanism of cinchona alkaloid carbamate-type receptors for 3,5-dinitrobenzoyl amino acids. Maier, N.M., Schefzick, S., Lombardo, G.M., Feliz, M., Rissanen, K., Lindner, W., Lipkowitz, K.B. J. Am. Chem. Soc. (2002) [Pubmed]
  13. Highly enantioselective conjugate addition of malonate and beta-ketoester to nitroalkenes: asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids. Li, H., Wang, Y., Tang, L., Deng, L. J. Am. Chem. Soc. (2004) [Pubmed]
  14. Asymmetric synthesis of alpha-amino acids via cinchona alkaloid-catalyzed kinetic resolution of urethane-protected alpha-amino acid N-carboxyanhydrides. Hang, J., Tian, S.K., Tang, L., Deng, L. J. Am. Chem. Soc. (2001) [Pubmed]
  15. Asymmetric synthesis of beta-hydroxy amino acids via aldol reactions catalyzed by chiral ammonium salts. Mettath, S., Srikanth, G.S., Dangerfield, B.S., Castle, S.L. J. Org. Chem. (2004) [Pubmed]
  16. Formation of disubstituted beta-lactones using bifunctional catalysis. Calter, M.A., Tretyak, O.A., Flaschenriem, C. Org. Lett. (2005) [Pubmed]
  17. Optosensor for cinchona alkaloids with C18 silica gel as a substrate. Gong, Z., Zhang, Z., Yang, X. The Analyst. (1997) [Pubmed]
  18. Direct STM investigation of cinchona alkaloid adsorption on Cu(III). Xu, Q.M., Wang, D., Han, M.J., Wan, L.J., Bai, C.L. Langmuir : the ACS journal of surfaces and colloids. (2004) [Pubmed]
 
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