Chiral ion pairs in catalysis: lithium salts of chiral metallocomplex anions as catalysts for asymmetric C-C bond formation

Tetrahedron Asymmetry

Volumn 20, Issue 15, 2009, Pages 1746-1752

  Belokon', Yuri N ^a   Maleev, Victor I ^a   Kataev, Dmitri A ^a   Saveleva, Tatiana F ^a   Skrupskaya, Tatiana V ^a   Nelyubina, Yulia V ^a   North, Michael ^b  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM SALT; METAL COMPLEX; SALICYLALDEHYDE; SCHIFF BASE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; MICHAEL ADDITION; PRIORITY JOURNAL;

EID: 69149102586     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.06.006     Document Type: Article

References (33)

1. Some recent references:. North M., Usanov D., and Young C. Chem. Rev. 108 (2008) 5146-5226 and references cited therein
2. Snyder S., Tang Z., and Gupta R. J. Am. Chem. Soc. 131 (2009) 5744-5745
3. Tone H., Buchotte M., Mordant C., Guittet E., Ayad T., and Ratovelmanana-Vidal V. Org. Lett. 11 (2009) 1995-1997
4. Lai H., Huang Z., Wu Q., and Qin Y. J. Org. Chem. 74 (2009) 283-288
5. Llewellyn D.B., Adamson D., and Arndtsen B.A. Org. Lett. 2 (2000) 4165-4168
6. Gonçalves-Faebos M.-H., Vial L., and Lacour J. Chem. Commun. 7 (2008) 829-831
7. Constant S., Tortoioli S., Muller J., Linder D., Buron F., and Lacour J. Angew. Chem., Int. Ed. 46 (2007) 8979-8982
8. Llewellyn D., and Arndtsen B. Organometallics 23 (2004) 2838-2840
9. Llewellyn D., and Arndsten B. Tetrahedron: Asymmetry 16 (2005) 1789-1799
10. Mayer S., and List B. Angew. Chem., Int. Ed. 45 (2006) 4393-4395
11. Wang X., and List B. Angew. Chem., Int. Ed. 47 (2008) 1119-1122
12. Mukherjee S., and List B. J. Am. Chem. Soc. 129 (2007) 11336-11337
13. Rueping M., Antonchick A.P., and Brinkmann C. Angew. Chem., Int. Ed. 46 (2007) 6903-6906 and references cited therein
14. Hamilton G.L., Kang E.J., Mba M., and Toste F.D. Science 317 (2007) 496-499
15. Shibasaki M. In: Fritz V., Staddart J., and Shibasaki M. (Eds). Asymmetric Two-center Catalysis. Simulating Concepts in Chemistry (2000), Wiley-VCH, New York 105-121
16. Holmes I.P., and Kagan H.B. Tetrahedron Lett. 41 (2000) 7453-7456
17. Hatano M., Ikeno T., Miyamoto T., and Ishihara K. J. Am. Chem. Soc 127 (2005) 10776-10777
18. Hatano M., Ikeno T., Matsumura T., Torii S., and Ishihara K. Adv. Synth. Catal. 350 (2008) 1776-1780
19. Ichibakase T., Orito Y., and Nakajima M. Tetrahedron Lett. 49 (2008) 4427-4429
20. Imahori T. In: Yamamoto H., and Ishihara K. (Eds). Li(I), Na(I) and K(I) Lewis Acids. Acid Catalysis in Modern Organic Synthesis (2008), Wiley-VCH, Weinheim 109-133
21. Moss S., King B., de Meijere A., Kozhushkov S., Eaton P., and Michl J. Org. Lett. 3 (2001) 2375
22. Volkis V., Mei H., Shoemaker R.K., and Michl J. J. Am. Chem. Soc. 131 (2009) 3132-3133
23. Belokon Y.N., Maleev V.I., Kataev D.A., Maĺfanov I.L., Bulychev A.G., Moskalenko M.A., Saveĺeva T.F., Skrupskaya T.V., Lyssenko K.A., Godovikov I.A., and North M. Tetrahedron: Asymmetry 19 (2008) 822-831
24. Λ- or Δ-Correspond, respectively, to left and right spiral arrangement of ligands in relation to the C2 axis of the complexes, according to Legg, J.; Douglas, B. J. Am. Chem. Soc. 1966, 88, 2697-2699.
25. Belokon Y., Belikov V., Vitt S., Saveleva T., Burbelo V., Bakhmutov V., Alexandrov G., and Struchkov Y. Tetrahedron 33 (1977) 2551
26. Burrows R., and Bailar J. J. Am. Chem. Soc. 88 (1966) 4150-4253
27. Tomioka K., Nagaoka Y., and Yamaguchi M. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Conjugate Addition Reactions. Comprehensive Asymmetric Catalysis Vol. 3 (1999), Springer, Berlin Chapter 31
28. Christoffers J., Koripelly G., Rosiak A., and Rössle M. Synthesis 9 (2007) 1279-1300
29. Almaşi D., Alonso D.A., and Nájera C. Tetrahedron: Asymmetry 18 (2007) 299-365
30. Sheldrick, G. shelxtl-97, Version 5.10, Bruker AXS: Madison, WI-53719, USA.
31. Manickam G., and Sundararajan G. Tetrahedron: Asymmetry 8 (1997) 2271-2278
32. Bauer H.F., and Drinkard W.C. J. Am. Chem. Soc. 88 (1966) 4150-4156
33. Çetinkaya B., Gümrükçü I., Lappert M.F., Atwood J.L., and Shakir R. J. Am. Chem. Soc. 102 (1980) 2086-2088