Novel and efficient insertions of carbons carrying O-, S-, and N-Linked substituents: Synthesis of α-alkoxyalkyl, α-(Alkylthio)alkyl, and α-(Carbazol-9-yl)alkyl ketones

Journal of Organic Chemistry

Volumn 61, Issue 21, 1996, Pages 7564-7570

  Katritzky, Alan R ^a   Xie, Linghong ^a   Serdyuk, Larisa ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001603551     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960840p     Document Type: Article

References (49)

1. Krow, G. R. Tetrahedron 1987, 43, 3.
2. Trost, B. M.; Mikhail, G. K. J. Am. Chem. Soc. 1987, 109, 4124.
3. Montana, J. G.; Phillipson, N.; Taylor, R. J. K. J. Chem. Soc., Chem. Commun. 1994, 2289.
4. (a) Abraham, W. D.; Bhupathy, M.; Cohen, T. Tetrahedron Lett. 1987, 28, 2203.
5. (b) Cohen, T.; Kuhn, D.; Falck, J. R. J. Am. Chem. Soc. 1975, 97, 4749.
6. Katritzky, A. R.; Yang, Z.; Moutou, J.-L. Tetrahedron Lett. 1995, 36, 841.
7. Loeschorn, C. A.; Nakajima, M.; McCloskey, P. J.; Anselme, J.-P. J. Org. Chem. 1983, 48, 4407.
8. (a) Satoh, T.; Mizu, Y.; Kawashima, T.; Yamakawa, K. Tetrahedron 1995, 51, 703.
9. (b) Satoh, T.; Itoh, N.; Gengyo, K.; Yamakawa, K. Tetrahedron Lett. 1992, 33, 7543.
10. (c) Satoh, T.; Hayashi, Y.; Mizu, Y.; Yamakawa, K. Tetrahedron Lett. 1992, 33, 7181.
11. (d) Satoh, T.; Fujii, T.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1990, 63, 1266.
12. (a) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. J. Org. Chem. 1994, 59, 4725.
13. (b) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Synthesis 1994, 1283.
14. Kim, S.; Lee, S. Tetrahedron Lett. 1991, 32, 6575.
15. Holmquist, C. R.; Roskamp, E. J. Tetrahedron Lett. 1992, 33, 1131.
16. (a) Labar, D.; Laboureur, J. L.; Krief, A. Tetrahedron Lett. 1982, 23, 983.
17. (b) Laboureur, J. L.; Krief, A. Tetrahedron Lett. 1984, 25, 2713.
18. Uemura, S.; Ohe, K.; Sugita, N. J. Chem. Soc., Chem. Commun. 1988, 111.
19. Liu, P.; Vandewalle, M. Tetrahedron 1994, 50, 7061.
20. Trost, B. M. Chem. Rev. 1978, 78, 363.
21. Knapp, S.; Trope, A. F.; Theodore, M. S.; Hirata, N.; Barchi, J. J. J. Org. Chem. 1984, 49, 608.
22. (a) Katritzky, A. R.; Rachwal, S.; Hitchings, G. J. Tetrahedron 1991, 47, 2683.
23. (b) Katritzky, A. R.; Yang, Z.; Cundy, D. J. Aldrichim. Acta 1994, 27, 31.
24. (c) Katritzky, A. R.; Lan, X.; Fan, W.-Q. Synthesis 1994, 445.
25. (d) Katritzky, A. R.; Lan, X. Chem. Soc. Rev. 1994, 363.
26. Katritzky, A. R.; Xie, L.; Toader, D.; Serdyuk, L. J. Am. Chem. Soc. 1995, 117, 12015.
27. Katritzky, A. R.; Rachwal, S.; Rachwal, B. J. Chem. Soc., Perkin Trans. 1 1987, 791.
28. Katritzky, A. R.; Rachwal, S.; Caster, K. C.; Mahni, F.; Law, K. W.; Rubio, O. J. Chem. Soc., Perkin Trans. 1 1987, 781.
29. Katritzky, A. R.; Lang, H.; Wang, Z.; Zhang, Z.; Song, H. J. Org. Chem. 1995, 60, 7619.
30. Katritzky, A. R.; Lang, H.; Wang, Z.; Lie, Z. J. Org. Chem. 1996, submitted.
31. Katritzky, A. R.; Yang, Z.; Cundy, D. J. Synth. Commun. 1993, 23, 3061.
32. Hanson, J. R. (Section 3.1); Rickborn, B. (Section 3.2 and 3.3); Coveney, D.J. (Section 3.4) In Comprehensive Organic Synthesis; Trost. B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, p 705.
33. Katritzky, A. R.; Toader, D.; Xie, L. J. Org. Chem. 1996, 61, 7571.
34. Prakash, O.; Saini, N.; Tanwar, M. P.; Moriarty, R. M. Contemp. Org. Synth. 1995, 121.
35. Labadie, J. W.; Tueting, D.; Stille, J. K. J. Org. Chem. 1983, 48, 4634.
36. Jung, M. E.; Abrecht, S. J. Org. Chem. 1988, 53, 423.
37. Katritzky, A. R.; Yang, Z.; Lam, J. N. J. Org. Chem. 1991, 56, 6917.
38. De Kimpe, N.; De Buyck, L.; Verhe, R.; Schamp, N. Chem. Ber. 1983, 116, 3631.
39. Hoppe, D.; Lussmann, J.; Jones, P. G.; Schmidt, D.; Sheldrick, G. M. Tetrahedron Lett. 1986, 27, 3591.
40. Adam, W.; Hadjiarapoglou, L.; Jager, V.; Seidel, B. Tetrahedron Lett. 1989, 30, 4223.
41. Chiba, T.; Okimoto, M. J. Org. Chem. 1992, 57, 1375.
42. Katritzky, A. R.; Xie, L.; Afridi, A. S.; Fan, W.-Q.; Kuzmierkiewicz, W. Synthesis 1993, 47.
43. Caputo, R.; Ferreri, C.; Palumbo, G. Synthesis 1989, 464.
44. Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976, 98, 4887.
45. Katritzky, A. R.; Yang, Z.; Lam, J. N. J. Org. Chem. 1991, 56, 2143.
46. Katritzky, A. R.; Jurczyk, S.; Rachwal, B.; Rachwal, S.; Shcherbakova, I.; Yannakopoulou, K. Synthesis 1892, 1295.
47. Padmanabhan, S.; Ogawa, T.; Suzuki, H. Bull. Chem. Soc. Jpn. 1989, 62, 1358.
48. Morel, G.; Marchand, E.; Foucaud, A. Synthesis 1980, 918.
49. Prelog, V.; Hahn, V.; Brauchli, H.; Beyerman, H. C. Helv. Chim. Acta 1944, 27, 1209.