A new P,S-chiral auxiliary derived from thioglucose. X-ray structure of a palladium 1,3-diphenylallyl complex with a strongly rotated allyl ligand

Organometallics

Volumn 15, Issue 10, 1996, Pages 2419-2421

  Albinati, Alberto ^a   Pregosin, Paul S ^a   Wick, Karin ^a  

^a ETH ZURICH   (Switzerland)

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Indexed keywords

EID: 3743127668     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950983m     Document Type: Article

References (36)

1. von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. Leutenegger, U.; Umbricht, C.; Fahrni, P.; von Matt, A.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Mueller, D.; Umbricht, B.; Weber, A.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
2. von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. Leutenegger, U.; Umbricht, C.; Fahrni, P.; von Matt, A.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Mueller, D.; Umbricht, B.; Weber, A.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
3. von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. Leutenegger, U.; Umbricht, C.; Fahrni, P.; von Matt, A.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Mueller, D.; Umbricht, B.; Weber, A.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
4. von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. Leutenegger, U.; Umbricht, C.; Fahrni, P.; von Matt, A.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Mueller, D.; Umbricht, B.; Weber, A.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
5. von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. Leutenegger, U.; Umbricht, C.; Fahrni, P.; von Matt, A.; Pfaltz, A. Tetrahedron 1992, 48, 2143. Mueller, D.; Umbricht, B.; Weber, A.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
6. Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493.
7. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. J. Chem. Soc., Chem. Commun. 1994, 1417. Andersson, P. G.; Harden, A.; Tanner, D.; Norrby, P. O. Chem. Eur. J. 1995, 1, 12.
8. Gamez, P.; Dunjic, B.; Fache, F.; Lemaire, M. J. Chem. Soc., Chem. Commun. 1994, 1417. Andersson, P. G.; Harden, A.; Tanner, D.; Norrby, P. O. Chem. Eur. J. 1995, 1, 12.
9. Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelein, M.; Huttner, G.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 1769.
10. Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelein, M.; Huttner, G.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 1769.
11. Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelein, M.; Huttner, G.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 1769.
12. Hiraswa, K.; Kawamata, M.; Hiroi, K. Yakugaku Zasshi 1994, 114(2), 111. Yamaguchi, M.; Shima, T.; Hida, M. Tetrahedron Lett. 1990, 31, 5049. Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron: Asymmetry 1991, 2, 663.
13. Hiraswa, K.; Kawamata, M.; Hiroi, K. Yakugaku Zasshi 1994, 114(2), 111. Yamaguchi, M.; Shima, T.; Hida, M. Tetrahedron Lett. 1990, 31, 5049. Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron: Asymmetry 1991, 2, 663.
14. Hiraswa, K.; Kawamata, M.; Hiroi, K. Yakugaku Zasshi 1994, 114(2), 111. Yamaguchi, M.; Shima, T.; Hida, M. Tetrahedron Lett. 1990, 31, 5049. Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron: Asymmetry 1991, 2, 663.
15. Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. 1995, 107, 2577. Trost, B. M.; Lee, C. B.; Weiss, J. M. J. Am. Chem. Soc. 1995, 117, 7247. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. Trost, B. M.; Organ, M. G. J. Am. Chem. Soc. 1994, 116, 10320.
16. Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. 1995, 107, 2577. Trost, B. M.; Lee, C. B.; Weiss, J. M. J. Am. Chem. Soc. 1995, 117, 7247. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. Trost, B. M.; Organ, M. G. J. Am. Chem. Soc. 1994, 116, 10320.
17. Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. 1995, 107, 2577. Trost, B. M.; Lee, C. B.; Weiss, J. M. J. Am. Chem. Soc. 1995, 117, 7247. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. Trost, B. M.; Organ, M. G. J. Am. Chem. Soc. 1994, 116, 10320.
18. Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem. 1995, 107, 2577. Trost, B. M.; Lee, C. B.; Weiss, J. M. J. Am. Chem. Soc. 1995, 117, 7247. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. Trost, B. M.; Organ, M. G. J. Am. Chem. Soc. 1994, 116, 10320.
19. Togni, A.; Venanzi, L. M. Angew. Chem. 1994, 33, 497. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062.
20. Togni, A.; Venanzi, L. M. Angew. Chem. 1994, 33, 497. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062.
21. 3/pentane.
22. 1 The ca. 88% ee (HPLC) is not an optimized result in that we have made no attempt to change temperature, solvent, or base.
23. Michalik, M.; Freier, T.; Schwarze, M.; Selke, R. Magn. Reson. Chem. 1995, 33, 835. Selke, R.; Facklam, C.; Foken, H.; Heller, H. Tetrahedron: Asymmetry 1993, 4, 369.
24. Michalik, M.; Freier, T.; Schwarze, M.; Selke, R. Magn. Reson. Chem. 1995, 33, 835. Selke, R.; Facklam, C.; Foken, H.; Heller, H. Tetrahedron: Asymmetry 1993, 4, 369.
25. Rajanbabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101.
26. w = 0.101, GOF = 2.994. Upon convergence the final Fourier difference showed no significant features.
27. 2 and finds (via the observed enantiomer) that the attack of the nucleophile occurs at the allyl terminus trans to phosphorus, so that it is germane that C(3), trans to phosphorus, is the carbon below the coordination plane. The carbon atoms C(1) and C(2) will eventually develop the double bond.
28. During the preparation of this paper we learned of structural studies from the groups of A. Pfaltz, M. Zehnder, and A. Togni describing rotated 1,3-diphenylallyl Pd complexes. None of these has a terminal allyl carbon as far below the coordination plane as does 2. The differences are at least several tenths of an angstrom, thus making 2 an extreme case.
29. Togni, A; Burckhardt, U.; Gramlich, V.; Pregosin, P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031.
30. These are exo and endo isomers, where these descriptors refer to the orientation of the central allyl C-H vector with respect to the substituted Cp ring. These diastereomeric complexes exchange slowly on the NMR time scale. For structural details on related isomers and applications of the 2-D exchange methodology see: Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5160. Herrmann, J.; Pregosin, P. S.; Salzmann, R.; Albinati, A. Organometallics 1995, 14, 3311. Pregosin, P. S.; Salzmann, R.; Togni, A. Organometallics 1995, 14, 842. Breutel, C.; Pregosin, P. S.; Salzmann, R.; Togni, A. J. Am. Chem. Soc. 1994, 116, 4067 and references therein.
31. These are exo and endo isomers, where these descriptors refer to the orientation of the central allyl C-H vector with respect to the substituted Cp ring. These diastereomeric complexes exchange slowly on the NMR time scale. For structural details on related isomers and applications of the 2-D exchange methodology see: Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5160. Herrmann, J.; Pregosin, P. S.; Salzmann, R.; Albinati, A. Organometallics 1995, 14, 3311. Pregosin, P. S.; Salzmann, R.; Togni, A. Organometallics 1995, 14, 842. Breutel, C.; Pregosin, P. S.; Salzmann, R.; Togni, A. J. Am. Chem. Soc. 1994, 116, 4067 and references therein.
32. These are exo and endo isomers, where these descriptors refer to the orientation of the central allyl C-H vector with respect to the substituted Cp ring. These diastereomeric complexes exchange slowly on the NMR time scale. For structural details on related isomers and applications of the 2-D exchange methodology see: Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5160. Herrmann, J.; Pregosin, P. S.; Salzmann, R.; Albinati, A. Organometallics 1995, 14, 3311. Pregosin, P. S.; Salzmann, R.; Togni, A. Organometallics 1995, 14, 842. Breutel, C.; Pregosin, P. S.; Salzmann, R.; Togni, A. J. Am. Chem. Soc. 1994, 116, 4067 and references therein.
33. These are exo and endo isomers, where these descriptors refer to the orientation of the central allyl C-H vector with respect to the substituted Cp ring. These diastereomeric complexes exchange slowly on the NMR time scale. For structural details on related isomers and applications of the 2-D exchange methodology see: Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5160. Herrmann, J.; Pregosin, P. S.; Salzmann, R.; Albinati, A. Organometallics 1995, 14, 3311. Pregosin, P. S.; Salzmann, R.; Togni, A. Organometallics 1995, 14, 842. Breutel, C.; Pregosin, P. S.; Salzmann, R.; Togni, A. J. Am. Chem. Soc. 1994, 116, 4067 and references therein.
34. Burckhardt, U.; Hintermann, L.; Schnyder, A.; Togni, A. Organometallics 1995, 14, 5415 and references therein.
35. An allyl complex of Pd(II) derived from a new chiral P,S,O-chiral ligand has just been prepared and also shows a pseudo-axial methyl group: Spencer, J.; Gramlich, V.; Haeusel, R.; Togni, A. Tetrahedron: Asymmetry 1996, 7, 41.
36. Pregosin, P. S. Unpublished results.