Manipulating the diastereoselectivity of ortholithiation in planar chiral ferrocenes

Organic Letters

Volumn 15, Issue 13, 2013, Pages 3334-3337

  Herbert, Simon A ^a,b   Castell, Dominic C ^a   Clayden, Jonathan ^b   Arnott, Gareth E ^a  

^a STELLENBOSCH UNIVERSITY   (South Africa)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FERROUS ION; LIGAND; LITHIUM DERIVATIVE; NITROGEN; OXAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; FERROUS COMPOUNDS; LIGANDS; LITHIUM COMPOUNDS; MOLECULAR STRUCTURE; NITROGEN; OXAZOLES; STEREOISOMERISM;

EID: 84880011109     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4013734     Document Type: Article

References (35)

1. Sutcliffe, O. B.; Bryce, M. R. Tetrahedron: Asymmetry 2003, 14, 2297-2325
2. Atkinson, R. C. J.; Gibson, V. C.; Long, N. J. Chem. Soc. Rev. 2004, 33, 313-328
3. Arrayás, R. G.; Adrio, J.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 7674-7715
4. Butler, I. R. Eur. J. Inorg. Chem. 2012, 4387-4406
5. Ferrocenes: Ligands, Materials and Biomolecules; Stepnicka, P., Ed.; Wiley: Chichester, 2008.
6. Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications; Dai, L.-X.; Hou, X. L., Eds.; Wiley-VCH: Weinheim, 2010.
7. Ferrocenes: Compounds, Properties & Applications (Chemical Engineering Methods and Technology); Philips, E. S., Ed.; Nova Science Publishers: New York, 2011.
8. Fouda, M. F. R.; Abd-Elzaher, M. M.; Abdelsamaia, R. A.; Labib, A. A. Appl. Organomet. Chem. 2007, 21, 613-625
9. Hillard, E. A.; Jaouen, G. Organometallics 2011, 30, 20-27
10. Roux, C.; Biot, C. Future Med. Chem. 2012, 4, 783-797
11. Metallinos, C.; John, J.; Zaifman, J.; Emberson, K. Adv. Synth. Catal. 2012, 354, 602-606
12. Barreiro, E. M.; Broggini, D. F. D.; Adrio, L. A.; White, A. J. P.; Schwenk, R.; Togni, A.; Hii, K. K. Organometallics 2012, 31, 3745-3754
13. Buergler, J. F.; Niedermann, K.; Togni, A. Chem.-Eur. J. 2012, 18, 632-640
14. Zirakzadeh, A.; Schuecker, R.; Gorgas, N.; Mereiter, K.; Spindler, F.; Weissensteiner, W. Organometallics 2012, 31, 4241-4250
15. Eitel, S. H.; Bauer, M.; Schweinfurth, D.; Deibel, N.; Sarkar, B.; Kelm, H.; Krüger, H.-J.; Frey, W.; Peters, R. J. Am. Chem. Soc. 2012, 134, 4683-4693
16. Gao, D.-W.; Shi, Y.-C.; Gu, Q.; Zhao, Z.-L.; You, S.-L. J. Am. Chem. Soc. 2013, 135, 86-89
17. Clayden, J. Top. Organomet. Chem. 2003, 5, 251-286
18. Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 1995, 74-76
19. Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419-1430
20. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79-81
21. Nishibayashia, Y.; Segawaa, K.; Arikawaa, Y.; Ohea, K.; Hidaib, M.; Uemura, S. J. Organomet. Chem. 1997, 545-546, 381-398
22. Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10-11
23. Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002-6003
24. Sammakia, T.; Latham, H. A. J. Org. Chem. 1996, 61, 1629-1635
25. Geisler, F. M.; Helmchen, G. J. Org. Chem. 2006, 71, 2486-2492
26. Özçubukçu, S.; Schmidt, F.; Bolm, C. Org. Lett. 2005, 7, 1407-1409
27. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937-4943
28. Overman, L. E.; Owen, C. E.; Zipp, G. G. Angew. Chem., Int. Ed. 2002, 41, 3884-3887
29. Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-W. Tetrahedron Lett. 1996, 37, 6137-6140
30. Herbert, S. A.; Arnott, G. E. Org. Lett. 2010, 12, 4600-4603
31. Chadwick, S. T.; Ramirez, A.; Gupta, L.; Collum, D. B. J. Am. Chem. Soc. 2007, 129, 2259-2268
32. Saá, J. Helv. Chim. Acta 2002, 85, 814-840
33. García, J. I.; García-Marín, H.; Mayoral, J. A.; Pérez, P. Green Chem. 2010, 12, 426-434
34. Attempting to correlate a linear free energy relationship with the steric bulk of the R-groups on the diglyme ligands was also unsuccessful, even when applying recent developments in this area; see: Harper, K. C.; Bess, E. N.; Sigman, M. S. Nat. Chem. 2012, 4, 366-374
35. No data exists regarding the nature of this species, but it is more than likely monomeric in solution. For DGME·LiHMDS monomer data, see: Lucht, B. L.; Bernstein, M. P.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 10707-10718