An unprecedented, tandem Aldol-Grob reaction sequence

Journal of Organic Chemistry

Volumn 63, Issue 19, 1998, Pages 6438-6439

  Kabalka, George W ^a   Tejedor, David ^a   Li, Nan Sheng ^a   Malladi, Rama R ^a   Trotman, Sarah ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001322019     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo981274w     Document Type: Article

References (35)

1. Kane, R. Ann. Physik chem. 1838, 44, 475
2. J. Prakt. Chem. 1838, 15, 129.
3. Wurtz, A. Buli. Soc. Chim. Fr. 1872, 17, 436;
4. Ber. 1872, 5, 326.
5. Nielsen, A. T.; Houlihan, W. J. Organic Reactions 1968, 16.
6. Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746.
7. Larock, R. C. Comprehensive Organic Transformations; VCH Publishers: New York: 1989; pp 167-172.
8. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
9. Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868.
10. Ramachandran, P. V.; Lu, Z.-H.; Brown, H. C. Tetrahedron Lett. 1997, 38, 761.
11. Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918.
12. Benedetti, F.; Miertus, S.; Norbedo, S.; Tossi, A.; Zlatoidzky, P. J. Org. Chem. 1997, 62, 9348.
13. Chemler, S. R.; Roush, W. R. J. Org. Chem. 1998, 63, 3800.
14. Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron: Asymmetry 1994, 5, 173
15. Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447.
16. Livant, P.; Xu, W. J. Org. Chem. 1998, 63, 636.
17. Kalaus, G.; Juhász, L; Greiner, L; Kajtár-Peredy, M.; Brlik, J.; Szabó, L.; Szántay, C. J. Org. Chem. 1997, 62, 9188.
18. Ramachandran, P. V.; Xu, W.-C; Brown, H. C. Tetrahedron Lett. 1997, 38, 769.
19. Abiko, A.; Liu, J.-F.; Masamune, S. J. Org. Chem. 1996, 61, 2590.
20. Duffy, J. L.; Yoon, T. P.; Evans, D. A. Tetrahedron Lett. 1995, 36, 9245.
21. Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 7346.
22. Narayana, C.; Reddy, M. R.; Hair, M.; Kabalka, G. W. Tetrahedron Lett. 1997, 38, 7705.
23. Presented in part at the 216th National Meeting of the American Chemical Society, Boston, MA, August 23-27, 1998; ORGN 210.
24. Williams, J. M. J. Preparation of Alkenes; Oxford University Press: New York, 1996.
25. Control experiments reveal that (Z)-l-phenyl-l-alkenes do not isomerize to the corresponding (E)-isomers under the reaction conditions.
26. Isomeric mixtures of syn- and antiβ-aryl-β-hydroxy ketones consistently yield (E)-alkenes.
27. Grob, C. A. Angew. Chem., Int. Ed. Eng. 1969, 8, 535.
28. Armesto, X. L.; Canle, M.; Losada, M.; Santaballa, J. A. J. Org. Chem. 1994, 59, 4659.
29. De Giacomo, M.; Bettolo, R. M.; Scarpelli, R. Tetrahedron Lett. 1997, 38, 3469.
30. Nagumo, A.; Matsukuma, A.; Inoue, F.; Yamamoto, T.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1990, 1538.
31. Yamamoto, H.; Sumune, H.; Sakai, K. Tetrahedron 1991, 47, 8523.
32. Amann, C. M.; Fisher, P. V.; Pugh, M. L.; West, F. G. J. Org. Chem. 1998, 63, 2806
33. Koch, T.; Bandemer, K.; Boland, W. Helv. Chim. Acta 1997, 80, 838.
34. Waldemar, A.; Biancafort, L. J. Org. Chem. 1997, 62, 1623.
35. Grove, J. J. C.; Holzapfel, C. W.; Williams, D. B. G. Tetrahedron Lett. 1996, 37, 5817.