Diphosphines containing stereogenic P atoms: Synthesis of (S,S)-C,C′-tetramethylsilanebis-(1-naphthylphenylphosphine) and applications in enantioselective catalysis

Organometallics

Volumn 17, Issue 4, 1998, Pages 668-675

  Stoop, Robert M ^a   Mezzetti, Antonio ^a   Spindler, Felix ^b  

^a ETH ZURICH   (Switzerland)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001538827     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970539e     Document Type: Article

References (46)

1. Vineyard B. D.; Knowles, W. S.; Sabacky, M. J.; Bachmann, G. L.; Weinkauff, D. J. J. Chem. Am. Soc. 1977, 99, 5946.
2. Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysis; VCH: Weinheim, Germany, 1993.
3. (a) Akutagawa, S. Appl. Catal. A: General 1995, 128, 171.
4. (b) Kumobayashi, H. Recl. Trav. Chim. Pays-Bas 1996, 115. 201.
5. (c) Togni, A.; Angew. Chem., Int. Ed. Engl. 1996, 35, 1475.
6. (d) See ref 10 in Burk et al.: Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142.
7. Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365.
8. Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375.
9. (a) Jugé S.; Stéphan, M.; Laffitte, J. A.; Genet, J. P. Tetrahedron Lett. 1990, 31, 6357.
10. (b) Jugé, S.; Merdès, R.; Stéphan, M.; Genêt, J. P. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 77, 199.
11. (c) Jugé, S.; Stéphan, M.; Merdès, R.; Genet, J. P.; Halut-Desportes, D. J. Chem. Soc., Chem. Commun. 1993, 531.
12. Carey, J. V.; Barker, M. D.; Brown, J. M.; Russell, M. J. H. J. Chem. Soc., Perkin Trans. 1 1993, 831.
13. Corey, E. J.; Zhuoliang, C.; Tanoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000.
14. Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Kazuhiko, S. J. Am. Chem. Soc. 1990, 112, 5244.
15. Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
16. (a) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Cano De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665.
17. (b) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Cano De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675.
18. (c) Genêt, J. P.; Jugé, S.; Laffitte, J. A.; Pinel, C.; Mallart, S. (Elf Aquitaine). PCT Int. Appl. WO 01390, 1994; Chem. Abstr. 1994, 121, P156763d.
19. 13 and, in the case of 1, refers to the uncoordinated ligand.
20. Cahn, R. S.; Ingold, C. K.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1966, 5, 385.
21. (a) Huffmann, J. C.; Skupinski, W. A.; Caulton, K. G. Cryst. Struct Commun. 1982, 11, 1435.
22. (b) Schmidbaur, H.; Wimmer, T.; Lachmann, J.; Müller, G. Chem. Ber. 1991, 124, 275.
23. (c) Schmidbaur, H.; Stützer, A.; Bissinger, P.; Schier, A. Z. Anorg. Allg. Chem. 1993, 619, 1519.
24. Jones, P. G. Acta Crystallogr. 1984, A43, 660.
25. 2 (Scheme 2).
26. 18 resulted in extensive decomposition of 1 to P(1-Np)(Ph)(Me) and other unidentified products.
27. McKinstry, L.; Livinghouse, T. Tetrahedron Lett. 1994, 35, 9319.
28. 1H NMR spectrum of a 1:1 mixture of (l)-1 and (u)-1, obtained by deprotection of a mixture of (l)- and (u)-2 with morpholine (Scheme 2).
29. Kyba, E. P.; Rines, S. P. J. Org. Chem. 1982, 47, 4800.
30. (a) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
31. (b) Rappé, A. K.; Colwell, K. S.; Casewit, C. J. Inorg. Chem. 1993, 32, 3438.
32. (a) Jung, C. W.; Garrou, P. E.; Huffman, P. R.; Caulton, K. G. Inorg. Chem. 1984, 23, 726.
33. (b) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155 and references therein.
34. Rossi, A. R.; Hoffmann, R. Inorg. Chem. 1975, 14, 365.
35. Jia, G.; Lee, I.; Meek, D. W.; Gallucci, J. C. Inorg. Chim. Acta 1990, 177, 81.
36. Zhu, G.; Cao, P.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 1799 and references cited therein.
37. Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207.
38. Yoshikuni T.; Bailar, J. C., Jr. Inorg. Chem. 1982, 21, 2129.
39. (a) Glaser, R.; Geresh, S.; Twaik, M. Tetrahedron 1978, 34, 3617.
40. (b) Buser, H. P.; Pugin, B.; Spindler, F.; Sutler, M. Tetrahedron 1991, 47, 5709.
41. Mezzetti, A.; Tschumper, A.; Consigho, G. J. Chem. Soc, Dalton Trans. 1995, 49 and references therein.
42. (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
43. (b) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062, and references therein.
44. 32
45. Nettekoven, U.; Widhalm, M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1997, 8, 3185.
46. Ito, K.; Harada, T.; Tai, A. Bull. Chem. Soc. Jpn. 1980, 53, 3367.