Dynamics of solvent exchange in organolithium reagents. Lithium as a center of chirality

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 273-274

  Reich, Hans J ^a   Kulicke, Klaus J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000339985     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953198+     Document Type: Article

References (33)

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3. (a) Reich, H. J.; Borst, J. P. J. Am. Chem. Soc. 1991, 133, 1835. Reich. H. J.: Borst, J. P.; Dykstra, R. R.; Green, D. P. J. Am. Chem. Soc. 1993, 115, 8728. Reich, H. J.; Borst, J. P.; Dykstra. R. R. Tetrahedron 1994, 50, 5869.
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12. Fraenkel. G.; Chow. A.; Winchester, W. R. J Am. Chem. Soc 1990, 112, 1382. Fraenkel. G.; Chow. A.; Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 6190. Fraenkel, G.; Pramanik, P J. Org. Chem. 1984, 49, 1314. Fraenkel, G.; Subramanian, S.; Chow, A. J. Am. Chem. Soc: 1995, 117, 6300-6307. Eppers, O.; Günther, H. Helv. Chim. Acta 1992, 75, 2553. Harder, S.; Boersma, J.; Brandsma, L.; Kanters, J. A.; Bauer. W., Schleyer, P. v. R.; Schollhom, H.; Thewalt, U. Organometallics 1989, 8, 1688.
13. Fraenkel. G.; Chow. A.; Winchester, W. R. J Am. Chem. Soc 1990, 112, 1382. Fraenkel. G.; Chow. A.; Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 6190. Fraenkel, G.; Pramanik, P J. Org. Chem. 1984, 49, 1314. Fraenkel, G.; Subramanian, S.; Chow, A. J. Am. Chem. Soc: 1995, 117, 6300-6307. Eppers, O.; Günther, H. Helv. Chim. Acta 1992, 75, 2553. Harder, S.; Boersma, J.; Brandsma, L.; Kanters, J. A.; Bauer. W., Schleyer, P. v. R.; Schollhom, H.; Thewalt, U. Organometallics 1989, 8, 1688.
14. Fraenkel. G.; Chow. A.; Winchester, W. R. J Am. Chem. Soc 1990, 112, 1382. Fraenkel. G.; Chow. A.; Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 6190. Fraenkel, G.; Pramanik, P J. Org. Chem. 1984, 49, 1314. Fraenkel, G.; Subramanian, S.; Chow, A. J. Am. Chem. Soc: 1995, 117, 6300-6307. Eppers, O.; Günther, H. Helv. Chim. Acta 1992, 75, 2553. Harder, S.; Boersma, J.; Brandsma, L.; Kanters, J. A.; Bauer. W., Schleyer, P. v. R.; Schollhom, H.; Thewalt, U. Organometallics 1989, 8, 1688.
15. Collum, D. B. Acc. Chem. Res. 1992, 25, 448.
16. 7Li quadrupolar relaxation rates: Jackman. L. M.; Scarmoutzos. M.; DeBrosse, C. W. J. Am. Chem. Soc. 1987, 109, 5355. X-ray crystal structures: Setzer. W. N.; Schleyer. P. v. R. Adv. Organomet. Chem. 1985, 24, 353.
17. 7Li quadrupolar relaxation rates: Jackman. L. M.; Scarmoutzos. M.; DeBrosse, C. W. J. Am. Chem. Soc. 1987, 109, 5355. X-ray crystal structures: Setzer. W. N.; Schleyer. P. v. R. Adv. Organomet. Chem. 1985, 24, 353.
18. 7Li quadrupolar relaxation rates: Jackman. L. M.; Scarmoutzos. M.; DeBrosse, C. W. J. Am. Chem. Soc. 1987, 109, 5355. X-ray crystal structures: Setzer. W. N.; Schleyer. P. v. R. Adv. Organomet. Chem. 1985, 24, 353.
19. 7Li quadrupolar relaxation rates: Jackman. L. M.; Scarmoutzos. M.; DeBrosse, C. W. J. Am. Chem. Soc. 1987, 109, 5355. X-ray crystal structures: Setzer. W. N.; Schleyer. P. v. R. Adv. Organomet. Chem. 1985, 24, 353.
20. Lucht, B. T.; Collum. D. B. J. Am. Chem. Soc. 1994, 116, 6009.
21. The activation parameters were estimated from line shape simulations which did not specifically include the effects of Li-P coupling.
22. + (ΔΔG° = -2.6 kcal/mol). Woodin, R. L.; Beauchamp. J. L. J. Am. Chem. Soc. 1978, 100, 501.
23. T number: Reichardï. C. Solvents and Solvent Effects in Organic Chemistry: VCH: New York, 1988; p 368. (d) SIP/CIP ratio: Chang, C. J.; Kiesel, R. F.; Hogen-Esch, T. E. J. Am. Chem. Soc. 1973, 95, 8446.
24. T number: Reichardï. C. Solvents and Solvent Effects in Organic Chemistry: VCH: New York, 1988; p 368. (d) SIP/CIP ratio: Chang, C. J.; Kiesel, R. F.; Hogen-Esch, T. E. J. Am. Chem. Soc. 1973, 95, 8446.
25. T number: Reichardï. C. Solvents and Solvent Effects in Organic Chemistry: VCH: New York, 1988; p 368. (d) SIP/CIP ratio: Chang, C. J.; Kiesel, R. F.; Hogen-Esch, T. E. J. Am. Chem. Soc. 1973, 95, 8446.
26. T number: Reichardï. C. Solvents and Solvent Effects in Organic Chemistry: VCH: New York, 1988; p 368. (d) SIP/CIP ratio: Chang, C. J.; Kiesel, R. F.; Hogen-Esch, T. E. J. Am. Chem. Soc. 1973, 95, 8446.
27. Jackson, M. D.; Gilkerson, W. R. J. Am. Chem. Soc. 1979, 101, 328.
28. For examples of the formation of enantioenriched lithium reagents by chiral solvation/complexation at lithium, see: Nozaki, H.; Aratani, T.; Toraya. T.; Noyori, R. Tetrahedron 1971, 27, 905. Seebach, D.; Crass. G.; Wilka, E. M.; Hilvert, D.; Brunner, E. Helv. Chim. Acta 1979, 62, 2695. Zschage, O.; Schwark, J.-R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 296. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708. Klute, W.; Dress, R.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1993, 1409. For examples of the asymmetric reactions of achiral organolithium reagents induced by chiral solvation/complexation at lithium, see: Tamioka. K. Synthesis 1990, 541.
29. For examples of the formation of enantioenriched lithium reagents by chiral solvation/complexation at lithium, see: Nozaki, H.; Aratani, T.; Toraya. T.; Noyori, R. Tetrahedron 1971, 27, 905. Seebach, D.; Crass. G.; Wilka, E. M.; Hilvert, D.; Brunner, E. Helv. Chim. Acta 1979, 62, 2695. Zschage, O.; Schwark, J.-R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 296. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708. Klute, W.; Dress, R.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1993, 1409. For examples of the asymmetric reactions of achiral organolithium reagents induced by chiral solvation/complexation at lithium, see: Tamioka. K. Synthesis 1990, 541.
30. For examples of the formation of enantioenriched lithium reagents by chiral solvation/complexation at lithium, see: Nozaki, H.; Aratani, T.; Toraya. T.; Noyori, R. Tetrahedron 1971, 27, 905. Seebach, D.; Crass. G.; Wilka, E. M.; Hilvert, D.; Brunner, E. Helv. Chim. Acta 1979, 62, 2695. Zschage, O.; Schwark, J.-R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 296. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708. Klute, W.; Dress, R.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1993, 1409. For examples of the asymmetric reactions of achiral organolithium reagents induced by chiral solvation/complexation at lithium, see: Tamioka. K. Synthesis 1990, 541.
31. For examples of the formation of enantioenriched lithium reagents by chiral solvation/complexation at lithium, see: Nozaki, H.; Aratani, T.; Toraya. T.; Noyori, R. Tetrahedron 1971, 27, 905. Seebach, D.; Crass. G.; Wilka, E. M.; Hilvert, D.; Brunner, E. Helv. Chim. Acta 1979, 62, 2695. Zschage, O.; Schwark, J.-R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 296. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708. Klute, W.; Dress, R.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1993, 1409. For examples of the asymmetric reactions of achiral organolithium reagents induced by chiral solvation/complexation at lithium, see: Tamioka. K. Synthesis 1990, 541.
32. For examples of the formation of enantioenriched lithium reagents by chiral solvation/complexation at lithium, see: Nozaki, H.; Aratani, T.; Toraya. T.; Noyori, R. Tetrahedron 1971, 27, 905. Seebach, D.; Crass. G.; Wilka, E. M.; Hilvert, D.; Brunner, E. Helv. Chim. Acta 1979, 62, 2695. Zschage, O.; Schwark, J.-R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 296. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708. Klute, W.; Dress, R.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1993, 1409. For examples of the asymmetric reactions of achiral organolithium reagents induced by chiral solvation/complexation at lithium, see: Tamioka. K. Synthesis 1990, 541.
33. For examples of the formation of enantioenriched lithium reagents by chiral solvation/complexation at lithium, see: Nozaki, H.; Aratani, T.; Toraya. T.; Noyori, R. Tetrahedron 1971, 27, 905. Seebach, D.; Crass. G.; Wilka, E. M.; Hilvert, D.; Brunner, E. Helv. Chim. Acta 1979, 62, 2695. Zschage, O.; Schwark, J.-R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 296. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708. Klute, W.; Dress, R.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1993, 1409. For examples of the asymmetric reactions of achiral organolithium reagents induced by chiral solvation/complexation at lithium, see: Tamioka. K. Synthesis 1990, 541.