Modification of the atropisomeric N,N-ligand 2,2′-di(pyridin-2-yl)-1,1′-binaphthalene and its application to the asymmetric allylation of benzaldehyde

Collection of Czechoslovak Chemical Communications

Volumn 68, Issue 5, 2003, Pages 865-884

  Charmant, Jonathan P H ^a   Hunt, Neil J ^a   Lloyd Jones, Guy C ^a   Nowak, Thorsten ^b  

^a Cantock's Close   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Asymmetric catalysis; Atropisomerism; Axially chiral ligands; Biaryls; Binaphthyls; Kumada cross coupling reaction; Pyridines; Resolution; Zinc complexes

Indexed keywords

2 (4 CHLOROPYRIDIN 2 YL) 2' (6 CHLOROPYRIDIN 2 YL); 2 (4 METHYLPYRIDIN 2 YL) 2' (6 METHYLPYRIDIN 2 YL); 2,2' BIS(4 CHLOROPYRIDIN 2 YL) 1,1' BINAPHTHALENE; 2,2' BIS(4 METHYLPYRIDIN 2 YL) 1,1' BINAPHTHALENE; 2,2' BIS(6 CHLOROPYRIDIN 2 YL); 2,2' BIS(6 METHYLPYRIDIN 2 YL); 2,2' BIS(PYRIDIN 2 YL) 1,1' BINAPHTHALENE; BENZALDEHYDE; NAPHTHALENE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHLORINATION; ENANTIOMER; ISOMER; METHYLATION; SYNTHESIS;

EID: 0038044645     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20030865     Document Type: Article

References (22)

1. Handy S. T.: Curr. Org. Chem. 2000, 4, 363.
2. McCarthy M., Guiry P. J.: Tetrahedron 2001, 57, 3809.
3. Charmant J. P. H., Fallis I. A., Hunt N. J., Lloyd-Jones G. C., Murray M., Nowak T.: J. Chem Soc., Dalton Trans. 2000, 11, 1723.
4. Joule J. A., Mills K., Smith G. F.: Heterocyclic Chemistry, p. 101. Chapman and Hall, London 1995.
5. Citterio A., Minisci F., Frachi V.: J. Org. Chem. 1980, 45, 4752.
6. Gros P., Fort Y., Caubere P.: J. Chem. Soc., Perkin Trans. 1 1997, 3071.
7. Mass spectroscopy of the product mixture suggested that some oxidative dimerisation of 1 had occurred.
8. Mongin O., Rocca P., Thomasditdumont L., Trecourt F., Marsais F., Godard A., Queguiner G.: J. Chem. Soc., Perkin Trans. 1 1995, 2503.
9. Abramovitch R. A., Knaus E. E.: J. Heterocycl. Chem. 1969, 6, 989.
10. Hanan G. S., Schubert U. S., Volkmer D., Riviere E., Lehn J. M., Kyritsakas N., Fischer J.: Can. J. Chem. 1997, 75, 169.
11. Gomez I., Alonso E., Ramon D. J., Yus M.: Tetrahedron 2000, 56, 4043.
12. Tamao K.: J. Organomet. Chem. 2002, 653, 23.
13. Chelucci G., Thummel R. P.: Chem. Rev. 2002, 102, 3129.
14. Fletcher N. C.: J. Chem. Soc., Perkin Trans. 1 2002, 1831.
15. Yanagisawa A., Nakashima H., Nakatsuka Y., Ishiba A., Yamamoto H.: Bull. Chem. Soc. Jpn. 2001, 74, 1129.
16. Cozzi P. G., Tagliavini E., UmaniRonchi A.: Gazz. Chim. Ital. 1997, 127, 247.
17. Cozzi P. G., Orioli P., Tagliavini E., UmaniRonchi A.: Tetrahedron Lett. 1997, 38, 145.
18. Kwong H. L., Lau K. M., Lee W. S., Wong W. T.: New J. Chem. 1999, 23, 629.
19. SAINT Integration Software. Siemens Analytical X-Ray Instruments Inc., Madison (WI) 1996.
20. Sheldrick G. M.: SADABS. A Program for Absorption Correction with the Siemens SMART System. University of Göttingen, Göttingen 1996.
21. SHELXTL Program System, version 5.1. Bruker Analytical X-Ray Instruments Inc., Madison (WI) 1998.
22. Corey E. J., Kim S. S.: Tetrahedron Lett. 1990, 31, 3715.