Synthesis and novel structure of the first crystallographically characterised chiral α-amino lithium alkoxide

Chemical Communications

Volumn , Issue 18, 1997, Pages 1721-1722

  Davies, John E ^a   Raithby, Paul R ^a   Snaith, Ronald ^a   Wheatley, Andrew E H ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002553170     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a703573j     Document Type: Article

References (35)

1. H. W. Gschwend and H. R. Rodriguez., Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem, Rev., 1990, 90, 879.
2. H. W. Gschwend and H. R. Rodriguez., Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem, Rev., 1990, 90, 879.
3. H. W. Gschwend and H. R. Rodriguez., Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem, Rev., 1990, 90, 879.
4. H. W. Gschwend and H. R. Rodriguez., Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem, Rev., 1990, 90, 879.
5. H. W. Gschwend and H. R. Rodriguez., Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem, Rev., 1990, 90, 879.
6. H. W. Gschwend and H. R. Rodriguez., Org. React., 1979, 26, 1; I. Omae, Chem. Rev., 1979, 79, 287; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63; V. Snieckus, Chem, Rev., 1990, 90, 879.
7. D. L. Comins and J. D. Brown, J. Org. Chem., 1984, 49, 1078 and references 2-10 therein.
8. D. L. Comins and J. D. Brown, Tetrahedron Lett., 1981, 22, 4213; D. L. Comins, J. D. Brown and N. B. Mantlo, Tetrahedron Lett., 1982, 23, 3979, D. L. Comins and J. D. Brown, J. Org. Chem., 1989, 54, 3730.
9. D. L. Comins and J. D. Brown, Tetrahedron Lett., 1981, 22, 4213; D. L. Comins, J. D. Brown and N. B. Mantlo, Tetrahedron Lett., 1982, 23, 3979, D. L. Comins and J. D. Brown, J. Org. Chem., 1989, 54, 3730.
10. D. L. Comins and J. D. Brown, Tetrahedron Lett., 1981, 22, 4213; D. L. Comins, J. D. Brown and N. B. Mantlo, Tetrahedron Lett., 1982, 23, 3979, D. L. Comins and J. D. Brown, J. Org. Chem., 1989, 54, 3730.
11. D. L. Comins and M. O. Killpack, J. Org. Chem., 1987, 52, 104.
12. (a) E. M. Arnett, M. A. Nichols and A. T. McPhail, J. Am. Chem. Soc., 1990, 112, 7059;
13. (b) M. A. Nichols, A. T. McPhail and E. M. Arnett, J. Am. Chem. Soc., 1991, 113, 6222;
14. (c) G. Hilmersson and Ö. Davidsson, J. Organomet. Chem., 1995, 489, 175; G. Hilmersson and Ö. Davidsson, Organometallics, 1995, 14, 912;
15. (c) G. Hilmersson and Ö. Davidsson, J. Organomet. Chem., 1995, 489, 175; G. Hilmersson and Ö. Davidsson, Organometallics, 1995, 14, 912;
16. (d) G. Hilmersson and Ö. Davidsson, J. Org. Chem., 1995, 60, 7660;
17. (e) H. J. Reich and K. J. Kulicke, J. Am. Chem. Soc., 1995, 117, 6621;
18. (f) J. M. Saá, G. Martorelli and A. Frontera, J. Org. Chem., 1996, 61, 5194;
19. (g) K. Sugasawa, M. Shindo, H. Noguchi and K. Koga, Tetrahedron Lett., 1996, 37, 7377.
20. A. Tatsukawa, K. Kawatake, S. Kanemasa and J. M. Rudzinski, J. Chem. Soc., Perkin Trans. 2, 1994, 2525; R. K. Dress, T. Rölle and R. W. Hoffmann, Chem. Ber., 1995, 128, 673; L. M. Pratt and I. M. Khan, Tetrahedron Lett., 1995, 6, 2165; G. Fraenkel, S. Subramanian and A. Chow, J. Am. Chem. Soc., 1995, 117, 6300.
21. A. Tatsukawa, K. Kawatake, S. Kanemasa and J. M. Rudzinski, J. Chem. Soc., Perkin Trans. 2, 1994, 2525; R. K. Dress, T. Rölle and R. W. Hoffmann, Chem. Ber., 1995, 128, 673; L. M. Pratt and I. M. Khan, Tetrahedron Lett., 1995, 6, 2165; G. Fraenkel, S. Subramanian and A. Chow, J. Am. Chem. Soc., 1995, 117, 6300.
22. A. Tatsukawa, K. Kawatake, S. Kanemasa and J. M. Rudzinski, J. Chem. Soc., Perkin Trans. 2, 1994, 2525; R. K. Dress, T. Rölle and R. W. Hoffmann, Chem. Ber., 1995, 128, 673; L. M. Pratt and I. M. Khan, Tetrahedron Lett., 1995, 6, 2165; G. Fraenkel, S. Subramanian and A. Chow, J. Am. Chem. Soc., 1995, 117, 6300.
23. A. Tatsukawa, K. Kawatake, S. Kanemasa and J. M. Rudzinski, J. Chem. Soc., Perkin Trans. 2, 1994, 2525; R. K. Dress, T. Rölle and R. W. Hoffmann, Chem. Ber., 1995, 128, 673; L. M. Pratt and I. M. Khan, Tetrahedron Lett., 1995, 6, 2165; G. Fraenkel, S. Subramanian and A. Chow, J. Am. Chem. Soc., 1995, 117, 6300.
24. T. Kottke and D. Stalke, J. Appl. Crystallogr., 1993, 26, 615.
25. G. M. Sheldrick, Acta Crystallogr., Sect. C. 1990, A46, 467.
26. G. M. Sheldrick, SHELXL-93, Program for Crystal Structure Refinement, University of Göttingen, 1993.
27. O. Graalmann, U. Klingebiel, W. Clegg, M. Haase and G. M. Sheldrick, Angew. Chem., 1984, 96, 904, Angew. Chem., Int. Edn. Engl., 1984, 23, 891; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032; S. C. Ball, I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147.
28. O. Graalmann, U. Klingebiel, W. Clegg, M. Haase and G. M. Sheldrick, Angew. Chem., 1984, 96, 904, Angew. Chem., Int. Edn. Engl., 1984, 23, 891; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032; S. C. Ball, I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147.
29. O. Graalmann, U. Klingebiel, W. Clegg, M. Haase and G. M. Sheldrick, Angew. Chem., 1984, 96, 904, Angew. Chem., Int. Edn. Engl., 1984, 23, 891; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032; S. C. Ball, I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147.
30. O. Graalmann, U. Klingebiel, W. Clegg, M. Haase and G. M. Sheldrick, Angew. Chem., 1984, 96, 904, Angew. Chem., Int. Edn. Engl., 1984, 23, 891; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032; S. C. Ball, I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147.
31. O. Graalmann, U. Klingebiel, W. Clegg, M. Haase and G. M. Sheldrick, Angew. Chem., 1984, 96, 904, Angew. Chem., Int. Edn. Engl., 1984, 23, 891; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032; S. C. Ball, I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147.
32. G. W. Klumpp, Rec. Trav. Chim. Pays-Bas, 1986, 105, 1.
33. M. Pink, G. Zahn and J. Sieler, Z. Allorg. Allg. Chem., 1994, 620, 749.
34. A. J. Edwards, M. A. Paver, P. R. Raithby, C. A. Russell and D. S. Wright, J. Chem. Soc., Dalton Trans., 1993, 3265.
35. A. Bax, R. H. Griffey and B. L. Hawkins, J. Magn. Reson., 1983, 55, 301.