Highly efficient ortho-fluoro-dimeric cinchona-derived phase-transfer catalysts

Tetrahedron Letters

Volumn 44, Issue 17, 2003, Pages 3497-3500

  Park, Hyeung Geun ^a   Jeong, Byeong Seon ^a   Yoo, Mi Sook ^a   Lee, Jeong Hee ^a   Park, Boon Saeng ^a   Kim, Myoung Goo ^a   Jew, Sang Sup ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CINCHONA ALKALOID; DIMER; FLUORINE DERIVATIVE; GLYCINE; PHENYL GROUP; QUATERNARY AMMONIUM DERIVATIVE;

ALKYLATION; ARTICLE; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; PHASE TRANSITION; SUBSTITUTION REACTION; SYNTHESIS;

CINCHONA;

EID: 0037459867     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00687-7     Document Type: Article

References (16)

1. Nelson A. Angew. Chem., Int. Ed. 38:1999;1583.
2. Shioiri T., Arai S. Vogtle F., Stoddart J.F., Shibasaki M. Stimulating Concepts in Chemistry. 2000;123-143 Wiley-VCH, Weinheim,
3. O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 10.
4. O'Donnell M.J. Aldrichim. Acta. 34:2001;3.
5. Dolling U.-H., Davis P., Grabowski E.J.J. J. Am. Chem. Soc. 106:1984;446.
6. O'Donnell M.J., Bennett W.D., Wu S. J. Am. Chem. Soc. 111:1989;2353.
7. Lygo B., Wainwright P.G. Tetrahedron Lett. 38:1997;8595.
8. Corey E.J., Xu F., Noe M.C. J. Am. Chem. Soc. 119:1997;12414.
9. For a recent report on the successful enantioselective monoalkylation of the glycinate imine 1, using chiral quaternary ammonium catalysts that are not derived from cinchona alkaloids, see: Ooi T., Kameda M., Maruoka K. J. Am. Chem. Soc. 121:1999;6519.
10. Jew S.-s., Jeong B.-S., Yoo M.-S., Huh H., Park H.-g. Chem. Commun. 2001;1244.
11. Park H.-g., Jeong B.-S., Yoo M.-S., Lee J.-H., Park M.-k., Lee Y.-J., Kim M.-J., Jew S.-s. Angew. Chem., Int. Ed. 41:2002;3036.
12. Very recently, the preparation and application of dimeric catalysts that incorporate a 9,10-dimethylanthracenyl bridge was reported by the C. Nájera group: Chinchilla R., Mazón P., Nájera C. Tetrahedron: Asymmetry. 13:2002;927.
13. Park H.-g., Jeong B.-S., Yoo M.-S., Park M.-k., Huh H., Jew S.-s. Tetrahedron Lett. 42:2001;4645.
14. Jew S.-s., Yoo M.-S., Jeong B.-S., Park I.Y., Park H.-g. Org. Lett. 4:2002;4245.
15. +: 874.4118, found: 874.4144.
16. 4-10.