Solution structures of a monodentate chiral lithium amide in the presence of lithium halide

Tetrahedron Letters

Volumn 37, Issue 41, 1996, Pages 7377-7380

  Sugasawa, Keizo ^a   Shindo, Mitsuru ^a   Noguchi, Hiroshi ^b   Koga, Kenji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030574042     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01681-4     Document Type: Article

References (27)

1. 1. For reviews, see: (a) Koga, K. J. Synth. Org. Chem. Jpn. 1990, 48, 463-475.
2. (b) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1-26.
3. (c) Koga, K. Pure Appl. Chem. 1994, 66, 1487-1492.
4. (d) Koga, K.; Shindo, M J. Synth. Org. Chem. Jpn. 1995, 53, 1021-1032.
5. 2. Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 495-498.
6. 3. (a) Majewski, M.; Gleave, D. M. J Org. Chem. 1992, 57, 3599-3605.
7. (b) Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533-534.
8. (c) Bunn, B. J.; Simpkins, N. S.;Spavold, Z.; Crimmin, M. J. J. Chem. Soc. Perkin Trans. 1 1993, 3113-3116.
9. (d) Majewski, M.; Lazny, R. Tetrahedron Lett. 1994, 35, 3653-3656.
10. (e) Majewski, M.; Lanzy, R.; Nowak, P. Tetrahedron Lett. 1995, 36, 5465-5468. For reviews, including discussion of salt effects, see
11. (f) Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624-1654.
12. (g) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290.
13. (h) Seebach, D.; Beck, A. K.; Studer, A. Modern Synthetic Methods Vol. 7; VCH: Weinheim, 1995; pp. 1-178.
14. 4. A small amount of LiCl could be released on mixing the lithium amide and TMSCl. See: Lipshutz, B. H.; Wood, M. R.; Lindsley, C. W. Tetrahedron Lett. 1995, 36, 4385-4388.
15. 5. Solution structures of bidentate chiral lithium amides were elucidated using the double labeling method. See (a) Sato, D.; Kawasaki, H.; Shimada, I.; Arata, Y.; Okamura, K.; Date, T.; Koga, K. J. Am. Chem. Soc. 1992, 114, 761-763.
16. (b) Aoki, K.; Noguchi, H.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1993, 34, 5105-5105.
17. 25+237°(benzene).
18. 7. (a) Galiano-Roth, A. S.; Kim, Y-J.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5053-5055.
19. (b) Hall, P. L.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9575-9585. For review,
20. (c) Collum, D. B. Acc. Chem. Res. 1993, 26, 227-234.
21. N-Li = 4.9 Hz).
22. 9. Homo dimer (B) was isolated as crystals from THF: Edwards, A. J.; Hockey, S.; Mair, F. S.; Raithby, P. R.; Snaith, R.; Simpkins, N. S. J. Org. Chem. 1993, 58, 6942-6943.
23. 10. Crystal structures of mixed aggregates of lithium amides and lithium chloride have been published. (a) Engelhardt, L. M.; Jacobsen, G. E.; White, A. H.; Raston, C. L. Inorg. Chem. 1991, 30, 3978-3980.
24. (b) Mair, F. S.; Clegg, W.; O'Neil, P. A. J. Am. Chem. Soc. 1993, 115, 3388-3389.
25. 12 See (a) Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1995, 117, 2166-2178.
26. (b) Henderson, K. W.; Dorigo, A. E.; Liu, Q-Y.; Williard, P. G.; Schleyer, P. v. R.; Bernstein, P. R. J. Am. Chem. Soc. 1996, 118, 1339-1347.
27. 12. Ireland, R. E.; Mueller, R. H., Williard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877.