Base-promoted 1,2-shifts in α-benzyloxy ketones

Tetrahedron Letters

Volumn 40, Issue 20, 1999, Pages 3823-3826

  Paquette, Leo A ^a   Zeng, Qingbei ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Carbanions; Enolates; Ketones; Rearrangements; Stereoselection

Indexed keywords

BASE; KETONE DERIVATIVE; LITHIUM; POTASSIUM HYDROXIDE;

ARTICLE; CHELATION; CHEMICAL MODIFICATION; DISSOCIATION; HEATING; ISOMERISM; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033553453     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00631-0     Document Type: Article

References (24)

1. [1] (a) Wittig, G.; Löhmann, L. Ann. 1942,550, 260.
2. (b) Wittig, G. Experientia 1958, 14, 389.
3. [2] Zimmerman, H. E. In de Mayo, P. Molecular Rearrangements, Volume 1; Interscience, N. Y.: 1963, pp 372-377.
4. [3] Dalrymple, D.L.; Kruger, T. L.; White, W. N. In Patai, S. Chemistry of the Ether Linkage; Interscience, N. Y.: 1967, pp 617-628.
5. [4] Lepley, A. R.; Guimanini, A. G. In Thyagarajan, B. S. Mechanism of Molecular Migrations. Volume 3; Interscience, N. Y.: 1971, pp 297-440.
6. [5] Hoffmann, R. W. Angew. Chem. 1979, 91, 625.
7. [6] (a) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105.
8. (b) Nakai, T.; Mikami, K. Chem. Rev. 1996, 86, 885.
9. [7] Marshall, J. A. In Trost, B. M.; Fleming, I.; Pattenden, G. Comprehensive Organic Synthesis, Volume 3; Pergamon, London: 1991, pp 975-1014.
10. [8] (a) Tomooka, K.; Yamamot, H.; Nakai, T. Liebigs Ann. Chem. 1997, 1275.
11. (b) Tomooka, K.; Yamamoto, H.; Nakai, T. J. Am. Chem. Soc. 1996, 118, 3317.
12. (c) Azzena, U.; Denurra, T.; Melloni, G.; Piroddi, A. M. J. Org. Chem. 1990,55, 5532.
13. (d) Evans, D. A.; Baillargeon, D. J. Tetrahedron Lett. 1978, 3315.
14. (e) Schäfer, H.; Schöllkopf, U.; Walter, D. Tetrahedron Lett. 1968, 2809.
15. [9] (a) Tomooka, K.; Igarashi, T.; Nakai, T. Tetrahedron 1994, 50, 5927.
16. (b) Tomooka, K.; Igarashi, T.; Nakai, T. Tetrahedron Lett. 1993, 34, 8139.
17. [10] Verner, E. J.; Cohen, T. J. Am. Chem. Soc. 1992, 114, 375.
18. [11] Hoffmann. R.; Brückner, R. Chem. Ber. 1992, 125, 1957.
19. [12] Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28, 1043.
20. [13] Maleczka, R. E., Jr.; Geng, F. J. Am. Chem. Soc. 1998, 120, 8551.
21. [14] (a) Curtin. D. Y.; Leskowitz, S. J. Am. Chem. Soc. 1951, 73, 2633.
22. (b) Curtin, D. Y.; Proops, W. R. J. Am. Chem. Soc. 1954, 76, 494.
23. 13C magnetic resonance spectra fully compatible with the structural assignments.
24. [16] Paquette, L. A.; Pegg, N. A.; Toops, D.; Maynard, G. D.; Rogers, R. D. J. Am. Chem. Soc. 1990, 112, 277.