Chiral aluminium complexes as phospho-transfer catalysts

Tetrahedron Letters

Volumn 40, Issue 23, 1999, Pages 4403-4406

  Duxbury, Julian P ^a   Cawley, Anthony ^a   Thornton Pett, Mark ^a   Wantz, Laurent ^a   Warne, Justin N D ^a   Greatrex, Robert ^a   Brown, Dearg ^b   Kee, Terence ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; PHOSPHORUS DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; MOLECULAR STABILITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033522933     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00738-8     Document Type: Article

References (38)

1. Smyth, M. S.; Ford, Jr., H.; Burke Jr., T. R. Tetrahedron Lett., 1992, 33, 4137; Hammerschmidt, F. Angew. Chem. Int. Ed. Engl., 1994, 33, 341; Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc., 1995, 117, 2931; Meier, C.; Laux, W. H. G. Tetrahedron, 1996, 52, 589; Jiao, X-Y.; Verbruggen, C.; Borloo, M.; Bollaert, W.; de Groot, A.; Dommisse, R.; Haemers, A. Synthesis, 1994, 23 and references therein.
2. Smyth, M. S.; Ford, Jr., H.; Burke Jr., T. R. Tetrahedron Lett., 1992, 33, 4137; Hammerschmidt, F. Angew. Chem. Int. Ed. Engl., 1994, 33, 341; Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc., 1995, 117, 2931; Meier, C.; Laux, W. H. G. Tetrahedron, 1996, 52, 589; Jiao, X-Y.; Verbruggen, C.; Borloo, M.; Bollaert, W.; de Groot, A.; Dommisse, R.; Haemers, A. Synthesis, 1994, 23 and references therein.
3. Smyth, M. S.; Ford, Jr., H.; Burke Jr., T. R. Tetrahedron Lett., 1992, 33, 4137; Hammerschmidt, F. Angew. Chem. Int. Ed. Engl., 1994, 33, 341; Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc., 1995, 117, 2931; Meier, C.; Laux, W. H. G. Tetrahedron, 1996, 52, 589; Jiao, X-Y.; Verbruggen, C.; Borloo, M.; Bollaert, W.; de Groot, A.; Dommisse, R.; Haemers, A. Synthesis, 1994, 23 and references therein.
4. Smyth, M. S.; Ford, Jr., H.; Burke Jr., T. R. Tetrahedron Lett., 1992, 33, 4137; Hammerschmidt, F. Angew. Chem. Int. Ed. Engl., 1994, 33, 341; Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc., 1995, 117, 2931; Meier, C.; Laux, W. H. G. Tetrahedron, 1996, 52, 589; Jiao, X-Y.; Verbruggen, C.; Borloo, M.; Bollaert, W.; de Groot, A.; Dommisse, R.; Haemers, A. Synthesis, 1994, 23 and references therein.
5. Smyth, M. S.; Ford, Jr., H.; Burke Jr., T. R. Tetrahedron Lett., 1992, 33, 4137; Hammerschmidt, F. Angew. Chem. Int. Ed. Engl., 1994, 33, 341; Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc., 1995, 117, 2931; Meier, C.; Laux, W. H. G. Tetrahedron, 1996, 52, 589; Jiao, X-Y.; Verbruggen, C.; Borloo, M.; Bollaert, W.; de Groot, A.; Dommisse, R.; Haemers, A. Synthesis, 1994, 23 and references therein.
6. Hilderbrand, R. L. (Ed.), The Role of Phosphonates in Living Systems, RCRC Press, Boca Raton, Fl., 1983; Engel, R. Chem. Rev., 1977, 77, 349; Blackburn, G. M. Chem. Ind., 1981, 134.
7. Hilderbrand, R. L. (Ed.), The Role of Phosphonates in Living Systems, RCRC Press, Boca Raton, Fl., 1983; Engel, R. Chem. Rev., 1977, 77, 349; Blackburn, G. M. Chem. Ind., 1981, 134.
8. Hilderbrand, R. L. (Ed.), The Role of Phosphonates in Living Systems, RCRC Press, Boca Raton, Fl., 1983; Engel, R. Chem. Rev., 1977, 77, 349; Blackburn, G. M. Chem. Ind., 1981, 134.
9. Smyth, M. S.; Ford, Jr., H.; Burke Jr., T. R. Tetrahedron Lett., 1992, 33, 4137.
10. Hammerschmidt, F. Angew. Chem. Int. Ed. Engl., 1994, 33, 341.
11. de Clercq, E.; Holy, A.; Rosenburg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P. C. Nature, 1986, 323, 464; Jennings, L. J.; Macchia, M.; Parkin, A. J. Chem. Soc., Perkin Trans. 1, 1992, 2197.
12. de Clercq, E.; Holy, A.; Rosenburg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P. C. Nature, 1986, 323, 464; Jennings, L. J.; Macchia, M.; Parkin, A. J. Chem. Soc., Perkin Trans. 1, 1992, 2197.
13. Lavielle, G.; Hautefaye, P.; Schaeffer, C.; Boutin, J. A.; Cudennec, C. A.; Pierré, A. J. Med. Chem., 1991, 34, 1998.
14. The best existing catalyst systems all exploit binaphthol: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem. Int. Ed. Engl., 1997, 36, 1236; Yokomatsu, T.; Yamagishi, T.; Matsumoto, K; Shibuya, S. Tetrahedron, 1996, 52, 11725; Rath, N. P.; Spilling, C. D. Tetrahedron Lett., 1994, 35, 227.
15. The best existing catalyst systems all exploit binaphthol: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem. Int. Ed. Engl., 1997, 36, 1236; Yokomatsu, T.; Yamagishi, T.; Matsumoto, K; Shibuya, S. Tetrahedron, 1996, 52, 11725; Rath, N. P.; Spilling, C. D. Tetrahedron Lett., 1994, 35, 227.
16. The best existing catalyst systems all exploit binaphthol: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem. Int. Ed. Engl., 1997, 36, 1236; Yokomatsu, T.; Yamagishi, T.; Matsumoto, K; Shibuya, S. Tetrahedron, 1996, 52, 11725; Rath, N. P.; Spilling, C. D. Tetrahedron Lett., 1994, 35, 227.
17. See for example; Hobday, M. D.; Smith, T. D. Coord. Chem. Rev., 1972, 9, 311; Serron, S. A.; Haar, C. M.; Nolan, S. P. Organometallics, 1997, 16, 5120; Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc., 1998, 120, 10780.
18. See for example; Hobday, M. D.; Smith, T. D. Coord. Chem. Rev., 1972, 9, 311; Serron, S. A.; Haar, C. M.; Nolan, S. P. Organometallics, 1997, 16, 5120; Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc., 1998, 120, 10780.
19. See for example; Hobday, M. D.; Smith, T. D. Coord. Chem. Rev., 1972, 9, 311; Serron, S. A.; Haar, C. M.; Nolan, S. P. Organometallics, 1997, 16, 5120; Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc., 1998, 120, 10780.
20. Davis, S. R.; Mitchell, M. C.; Cain, C. P.; Devitt, P. G.; Taylor, R. J.; Kee, T. P. J. Organomet. Chem., 1998, 550, 29.
21. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. Tetrahedron Lett., 1998, 39, 5485.
22. 13
23. 13
24. 13
25. Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem., 1994, 59, 1939.
26. Devitt, P. G.; Mitchell, M. C.; Weetman, J. M.; Taylor, R. J. Kee, T. P. Tetrahedron: Asymmetry, 1995, 6, 2039; Cawley, A.; Duxbury, J. P.; Kee, T. P. Tetrahedron:Asymmetry, 1998, 9, 1947.
27. Devitt, P. G.; Mitchell, M. C.; Weetman, J. M.; Taylor, R. J. Kee, T. P. Tetrahedron: Asymmetry, 1995, 6, 2039; Cawley, A.; Duxbury, J. P.; Kee, T. P. Tetrahedron: Asymmetry, 1998, 9, 1947.
28. A full package of structural information has been deposited with the Cambridge Crystallographic Data Centre.
29. Atwood, D. A.; Jegier, J. A.; Rutherford, D. Inorg. Chem., 1996, 35, 63.
30. Harris, R. K.; Mann, B. E. (Eds.), NMR and the Periodic Table, Academic Press, London, 1978, Ch. 9.
31. 2CPh) but otherwise does not require pre-drying. DMHP - dimethyl-H-phosphonate.
32. Zymanczyk-Duda, E.; Skwarczynski, M; Lejczak, B; Kafarski, P. Tetrahedron: Asymmetry, 1996, 7, 1277.
33. Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc., 1998, 120, 5315.
34. 21
35. Yokamatsu, T.; Yamagishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1, 1997, 1527.
36. Achiral [SALEN]AlR compounds react in moist solvent to afford [SALEN]Al(OH); thus (A) may result from DMHP and either methyl or hydroxide. Gurian, P. I.; Cheatham, L. K.; Ziller, J. W.; Barren, A. R. J. Chem. Soc., Dalton Trans. 1991, 1449.
37. Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc., 1998, 120, 10780.
38. Lopez, J.; Liang, S.; Bu, X. R. Tetrahedron Lett., 1998, 39, 4199.