Highly diastereoselective ortho-lithiation of chiral ferrocenecarboxamides

Tetrahedron Asymmetry

Volumn 21, Issue 15, 2010, Pages 1845-1854

  Stavrakov, Georgi ^a,b   Philipova, Irena ^a   Ivanova, Bojidarka ^c   Dimitrov, Vladimir ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^b MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

^c UNIVERSITY OF SOFIA   (Bulgaria)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CAMPHENE; ELECTROPHILE; FERROCENE DERIVATIVE;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LITHIATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SCREENING; STEREOCHEMISTRY;

EID: 77957557394     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.06.027     Document Type: Article

References (43)

1. Clayden, J.; Davies, R. P.; Hendy, M. A.; Snaith, R.; Wheatley, A. E. H. Angew. Chem., Int. Ed. 2001, 40, 1238-1240
2. Tilly, D.; Fu, J.; Zhao, B.; Alessi, M.; Castanet, A.; Snieckus, V.; Mortier, J. Org. Lett. 2010, 12, 68-71
3. Popovici, C.; Ona-Burgos, P.; Fernandez, I.; Roces, L.; Garcia-Granda, S.; Iglesias, M. H.; Ortiz, F. L. Org. Lett. 2010, 12, 428-431
4. Pradhan, T. K.; Ghosh, S. C.; De, A. Arkivoc 2003, ix, 158-173.
5. Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306-312
6. Beak, P.; Hunter, J. E.; Jun, Y. M. J. Am. Chem. Soc. 1983, 105, 6350-6351
7. Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356-363
8. Snieckus, V. Chem. Rev. 1990, 90, 879-933
9. Clayden, J. Organolithiums: Selectivity for Synthesis; Elsevier Science Ltd: Oxford, 2002. Chapter 2.3, pp 28- 73.
10. Togni, A.; Hayashi, T. Ferrocenes-Homogeneous Catalysis, Organic Synthesis, Material Science; Wiley-VCH: Weinheim, 1995
11. Togni, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1475-1477
12. Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407
13. Ueberbacher, B. J.; Griengl, H.; Weber, H. Chem. Commun. 2008, 3287-3289
14. Chiral Ferrocenes in Asymmetric Catalysis: Dai, L. X., Hou, X. L., Eds.; Wiley-VCH: Weinheim, 2009.
15. Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389-5393.
16. Rebiere, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568-570
17. Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835-5836
18. Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74-76
19. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79-81
20. Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10
21. Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002-6003
22. Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733-6745
23. Enders, D.; Peters, R.; Lochtman, R. Synlett 1997, 1462-1464
24. Zhang, W.; Shimanuki, T.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Org. Chem. 1999, 64, 6247-6351
25. Locke, A. J.; Pickett, T. E.; Richards, C. J. Synlett 2001, 141-143
26. Peters, R.; Fischer, D. F. Org. Lett. 2005, 7, 4137-4140
27. Vinci, D.; Mateus, N.; Wu, X.; Hancock, F.; Steiner, A.; Xiao, J. Org. Lett. 2006, 8, 215-218
28. Ferber, B.; Top, S.; Herson, P.; Jaouen, G. Organometallics 2007, 26, 1686-1691.
29. Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685-686
30. Laufer, R. S.; Veith, U.; Taylor, N. J.; Snieckus, V. Org. Lett. 2000, 2, 629-631
31. Metallinos, C.; Szillat, H.; Taylor, N.; Snieckus, V. Adv. Synth. Catal. 2003, 345, 370-382.
32. Stavrakov, G.; Simova, S.; Dimitrov, V. Tetrahedron: Asymmetry 2008, 19, 2119-2122.
33. Carman, R. M.; Greenfield, K. L. Aust. J. Chem. 1984, 37, 1785-1790
34. Ipaktschi, J. Chem. Ber. 1984, 117, 856-858.
35. Chen, Y. K.; Jeon, S.; Walsh, P. J.; Nugent, W. A. Org. Synth. 2005, 82, 87-92
36. Cheng, G.; Shei, C.; Sung, K. Chirality 2007, 19, 235-238.
37. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849-3862.
38. van Staveren, D. R.; Weyhermüller, T.; Metzler-Nolte, N. Dalton Trans. 2003, 2, 210-220.
39. Smith, C. R.; RajanBabu, T. V. Org. Lett. 2008, 10, 1657-1659.
40. Due to overlapping in the 1H NMR of the crude product with signals of the major isomer, only characteristic signals can be given for the minor diastereoisomer (Sp)-12b: 1H NMR (CDCl3, 600 MHz) d = 1.01 (s, 3H, 8-H), 1.97 (d, JH,H = 4.0 Hz. 1H, 4-H), 2.10 (s, 3H, Cp-CH3), 3.80 (d, JH,H = 7.4 Hz, 1H, 3- H), 4.06 (t, JH,H = 2.4 Hz, 1H, Cp-H), 4.20 (s, 5H, Cp5), 4.32-4.33 (m, 1H, Cp-H), 4.36-4.37 (m, 1H, Cp-H) ppm.
41. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008 64 112-122.
42. Blessing, R. H. Acta Crystallogr., Sect. A. 1995 1 33-38.
43. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13.