Reactions of Tempo with Alkylsamarium and Other Organometallic Reagents

Synlett

Volumn 1996, Issue 4, 1996, Pages 330-332

  Nagashima, Tadamichi ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001960207     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5426     Document Type: Article

References (29)

1. Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J Org. Chem. 1988, 55, 1629.
2. Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J Org. Chem. 1988, 55, 1629.
3. Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J Org. Chem. 1988, 55, 1629.
4. Newcomb, M. Tetrahedron 1993, 49, 1151. Beckwith, A. L. J.; Bowry, V. W. J. Am. Chem. Soc. 1994, 116, 2710.
5. Newcomb, M. Tetrahedron 1993, 49, 1151. Beckwith, A. L. J.; Bowry, V. W. J. Am. Chem. Soc. 1994, 116, 2710.
6. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196.
7. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196.
8. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271.
9. Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876 and references 3 and 4.
10. 2 is reported: Molander, G. A.; McKie, J. A. J. Org. Chem. 1992, 57, 3132.
11. Whitesides, G. M.; Newirth, T. L. J. Org. Chem. 1975, 40, 3448.
12. Sholle, V. D.; Golubev, V. A.; Rozantsev, E. G. Dokl. Akad. Nauk SSSR 1971, 200, 137; Chem. Abstr. 1972, 76, 25049e.
13. Sholle, V. D.; Golubev, V. A.; Rozantsev, E. G. Dokl. Akad. Nauk SSSR 1971, 200, 137; Chem. Abstr. 1972, 76, 25049e.
14. Hexyllithium (2.0 M in hexane) was purchased from Aldrich.
15. Hexylmagnesium bromide (2.0 M in ether) was purchased from Aldrich.
16. Hexyltitanium triisopropoxide was prepared from hexyllithium and chlorotitanium triisopropoxide: Weidmann, B.; Widler, L.; Olivero, A. G.; Maycok, C. D.; Seebach, D. Helv. Chim. Acta 1981, 64, 357.
17. Hexyl(chloro)zirconocene was prepared from hexyllithium and zirconocene dichloride at -78°C.
18. Reactions of alkyl(chloro)zirconocene and oxygen are reported to give corresponding alcohols: Blackburn, T. F.; Labinger, J. A.; Schwartz, J. Tetrahedron Lett. 1975, 35, 3041.
19. Paleos, C. M.; Karayannis, N. M.; Labes, M. M. J. Chem. Soc., Chem. Commun. 1970, 195.
20. Knochel, P. Synlett 1995, 393.
21. 2: Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, p 211.
22. Lipshutz, B. H.; Siegmann, K.; Garcia, E; Kayser, F. J. Am. Chem. Soc. 1993, 115, 9276 and references therein.
23. 2 (0.1 M in THF, 2.2 equiv) and HMPA (9 equiv) at 23°C: Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 114, 6050.
24. 2O = 10/1) to give Tempo adduct 9 (0.11 g, 0.38 mmol, 79%).
25. 2-HMPA see: Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717.
26. Cyclohexyl iodide also gave a low yield in copper catalyzed organosamarium 1,4-addition reaction: Wipf, P.; Venkatraman, S. J. Org. Chem. 1993, 58, 3455.
27. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
28. Berk, S. C.; Knochel, P.; Yeh, M. C. P. J. Org. Chem. 1988, 53, 5789.
29. Tempo was purchased from Aldrich, and was used as received.