Regiochemical observations depending on electrophiles in directed lithiation of 1,3-diheteroatom substituted arene tricarbonylchromium complexes

Tetrahedron

Volumn 65, Issue 4, 2009, Pages 752-756

  Michon, Christophe ^a   Murai, Masato ^a   Nakatsu, Mai ^a   Uenishi, Jun'ichi ^a   Uemura, Motokazu ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIUM DERIVATIVE; ELECTROPHILE; TRICARBONYL(1,7 DIMETHOXY 6 FORMYLTETRALINE)CHROMIUM; TRICARBONYL(1,7 DIMETHOXY 8 BROMOTETRALINE)CHROMIUM; TRICARBONYL(2 BROMO 3 CHLOROANISOLE)CHROMIUM; TRICARBONYL(2 CHLORO 3 METHOXYBENZALDEHYDE)CHROMIUM; TRICARBONYL(2 FORMYL 3 METHOXYBENZALDEHYDE ETHYLENEACETAL)CHROMIUM; TRICARBONYL(2,6 DIMETHOXYBENZALDEHYDE)CHROMIUM; TRICARBONYL(2,6 DIMETHOXYBROMOBENZENE)CHROMIUM; TRICARBONYL(4 CHLORO 2 METHOXYBENZALDEHYDE)CHROMIUM; TRICARBONYL(4 FORMYL 3 METHOXYBENZALDEHYDE ETHYLENEACETAL)CHROMIUM; TRICARBONYL(4 METHOXYCARBONYL 3 METHOXYBENZALDEHYDE ETHYLENEACETAL)CHROMIUM; TRICARBONYL(4 N,N DIMETHYLAMINOCARBONYL 3 METHOXYBENZALDEHYDE ETHYLENEACETAL)CHROMIUM; TRICARBONYL(METHYL 2 BROMO 3 METHOXYBENZYLETHER) CHROMIUM; TRICARBONYL(METHYL 2 FORMYL 3 METHOXYBENZYLETHER)CHROMIUM; TRICARBONYL(METHYL 4 FORMYL 3 METHOXYBENZYLETHER)CHROMIUM; TRICARBONYL[2 (ALPHA HYDROXYBENZYL) 3 METHOXYBENZALDEHYDE ETHYLENEACETAL]CHROMIUM; TRICARBONYL[2 ETHOXYCARBONYL 3 METHOXYBENZALDEHYDE ETHYLENEACETAL)CHROMIUM; UNCLASSIFIED DRUG;

ARTICLE; LITHIATION; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 57649108146     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.056     Document Type: Article

References (63)

1. Representative reviews;
2. Snieckus V. Chem. Rev. 90 (1990) 879
3. Whisler M.C., MacNeil S., Snieckus V., and Beak P. Angew. Chem., Int. Ed. 43 (2004) 2206
4. Schlosser M. Angew. Chem., Int. Ed. 44 (2005) 376
5. Gschwend, H.W.; Rodriguez, H.R. Organic Reactions; 1979; Vol. 26, p 1;
6. Clayden J. In: Rappoport Z., and Marek I. (Eds). Directed Metallation of Aromatic Compounds in the Chemistry of Organolithium Compounds (2004), John Wiley & Sons, Chichester, UK part 1, p 495
7. Hartung C.G., and Snieckus V. In: Astruc D. (Ed). Modern Arene Chemistry (2002), Wiley, VCH, Weinheim, Germany p 330
8. For some representative references;
9. McCarthy M., and Guiry P.J. Tetrahedron 57 (2001) 3809
10. Noyori R., and Takaya H. Acc. Chem. Res. 23 (1990) 345
11. Hubbard B.K., and Walsh C.T. Angew. Chem., Int. Ed. 42 (2003) 730
12. For some representative reviews:
13. Solladié-Cavallo A. In: Liebeskind L.S. (Ed). Advances in Metal-Organic Chemistry Vol. 1 (1989), JAI, Greenwich p 99
14. Davies S.G., Coote S.J., and Goodfellow C.L. In: Liebeskind L.S. (Ed). Advances in Metal-Organic Chemistry Vol. 2 (1991), JAI, Greenwich p 1
15. Uemura M. In: Liebeskind L.S. (Ed). Advances in Metal-Organic Chemistry Vol. 2 (1991), JAI, Greenwich p 195
16. Semmelhack M.F. In: Abel E.D., Stone F.G.A., and Wilkinson (Eds). Comprehensive Organometallic Chemistry II Vol. 12 (1995), Pergamon, Oxford p 979
17. Davies S.G., and McCarthy T.D. In: Abel E.D., Stone F.G.A., and Wilkinson (Eds). Comprehensive Organometallic Chemistry II Vol. 12 (1995), Pergamon, Oxford p 1039
18. In: Kündig E.P. (Ed). Transition Metal Arene π-Complexes in Organic Synthesis and Catalysis. Topics in Organometallic Chemistry Vol. 7 (2004), Springer, Berlin
19. Uemura, M. Organic Reactions; 2006; Vol. 67, p 217.
20. Some representative references on directed lithiation of arene chromium complexes;
21. Semmelhack M.F. In: Abel E.D., Stone F.G.A., and Wilkinson (Eds). Comprehensive Organometallic Chemistry II Vol. 12 (1995), Pergamon, Oxford p 1017
22. Berger A., Djukic J.-P., and Michon C. Coord. Chem. Rev. 225 (2002) 215
23. Dickens P.J., Gilday J.P., Negri J.T., and Widdowson D.A. Pure Appl. Chem. 62 (1990) 575
24. Some representative enantioselective lithiation;
25. Price D.A., Simpkins N.S., MacLeod A.M., and Watt A.P. J. Org. Chem. 59 (1994) 1961
26. Ewin R.A., MacLeod A.M., Price D.A., Simpkins N.S., and Watt A.L. J. Chem. Soc., Perkin Trans. 1 (1997) 401
27. Kündig E.P., and Quattropani A. Tetrahedron Lett. 35 (1994) 3497
28. Uemura M., Hayashi Y., and Hayashi Y. Tetrahedron: Asymmetry 5 (1994) 1427
29. Wihelm R., Sebhat I.K., White A.J.P., Williamis D.J., and Widdowson D.A. Tetrahedron: Asymmetry 11 (2000) 5003
30. Some representative diastereoselective lithiation:
31. Han J.W., Son S.K., and Chung Y.K. J. Org. Chem. 62 (1997) 8264
32. Alexakis A., Kanger T., Mangeney P., Rose-Munch F., Perrotey A., and Rose E. Tetrahedron: Asymmetry 6 (1995) 47
33. Kondo Y., Green J.R., and Ho J. J. Org. Chem. 58 (1993) 6182
34. Bolm C., Muñiz K., and Ganter C. New J. Chem. (1998) 1371
35. Michon C., Liu S., Hiragushi S., Uenishi J., and Uemura M. Synlett (2008) 1321
36. Tricarbonylchromium complexes of 3-methoxybenzaldehyde ethyleneacetal and the related arenes are lithiated at 2-position;
37. Kamikawa K., Watanabe T., and Uemura M. J. Org. Chem. 61 (1996) 1375
38. Watanabe T., Shakadou M., and Uemura M. Inorg. Chim. Acta 296 (1999) 80
39. Watanabe T., Shakadou M., and Uemura M. Synlett (2000) 1141
40. However, 3-methoxybenzylalcohol chromium complex and the related chromium complexes are predominantly lithiated at 4-position;
41. Uemura M., Nishikawa N., and Hayashi Y. Tetrahedron Lett. 21 (1980) 2069
42. Uemura M., Nishikawa N., Take K., Ohnishi M., Hirotsu K., Higuchi T., and Hayashi Y. J. Org. Chem. 48 (1983) 2349
43. Representative references;
44. Shimano M., and Meyers A.I. J. Am. Chem. Soc. 116 (1994) 10815
45. Slocum D.W., and Jennings C.A. J. Org. Chem. 41 (1976) 3653
46. Katsoulos G., Takagishi S., and Schlosser M. Synlett (1991) 731
47. Marzi E., Mongin F., Spitaleri A., and Schlosser M. Eur. J. Org. Chem. (2001) 2911
48. Schlosser M., and Marull M. Eur. J. Org. Chem. (2003) 1569
49. Winkle M.R., and Ronald R.C. J. Org. Chem. 47 (1982) 2101
50. Skowronska-Ptasinska M., Verboom W., and Reinhoudt D.N. J. Org. Chem. 50 (1985) 2690
51. Nguyen T.-H., Chau N.T.T., Castanet A.-S., Nguyen K.P.P., and Mortier J. J. Org. Chem. 72 (2007) 3419
52. Nguyen T.-H., Chau N.T.T., Castanet A.-S., Nguyen K.P.P., and Mortier J. Org. Lett. 7 (2005) 2445
53. Maggi R., and Schlosser M. J. Org. Chem. 61 (1996) 5430
54. Ribéreau P., and Queguiner G. Tetrahedron 40 (1984) 2107
55. Kasahara, I.; Sugiura, T.; Inoue, T. PCT Int. App. W09700845
56. (. Chem. Abstr. 126 (1997) 143985F9 )
57. Burton A.J., Cardwell K.S., Fuchter M.J., Lindvall M.K., Patel R., Packham T.W., Prodger J.C., Schilling M.B., and Walker M.D. Tetrahedron Lett. 44 (2003) 5653
58. Schmalz H.-G., Volk T., and Bernicke D. Tetrahedron 53 (1997) 9219
59. O-Lithiated amino acetal generated from benzaldehyde chromium complex with chiral lithium amide is performed by enantioselective ortho lithiation with BuLi and electrophilc substitution followed by acidic hydrolysis to give enantiomerically enriched ortho substituted benzaldehyde chromium complex. The formyl group in this case was not eliminated due to less steric hindrance;. Alexakis A., Kanger T., Mangeney P., Rose-Munch F., Perrotey A., and Rose E. Tetrahedron: Asymmetry 6 (1995) 2135
60. Dilithiated species of arene chromium complexes; see references
61. Davies S.G., Loveridge T., and Clough J.M. J. Chem. Soc., Chem. Commun. (1995) 817
62. Tan Y.-L., Widdowson D.A., and Wilhelm R. Synlett (2001) 1632
63. Quattropani A., Bernardinelli G., and Kündig E.P. Helv. Chim. Acta 82 (1992) 90