StePHOX, a new family of optically active, tunable phosphine-oxazoline ligands: syntheses and applications

Tetrahedron

Volumn 62, Issue 49, 2006, Pages 11470-11476

  Trudeau, Stéphane ^a   Morken, James P ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLINE DERIVATIVE; PHOSPHINE DERIVATIVE;

ALLYLATION; ARTICLE; CHIRALITY; DIHYDROXYLATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 33750436924     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.05.043     Document Type: Article

References (56)

1. For a review of catalytic asymmetric reactions using PHOX ligands, see:. Helmchen G., and Pfaltz A. Acc. Chem. Res. 33 (2000) 336
2. von Matt P., and Pfaltz A. Angew. Chem., Int. Ed. Engl. 32 (1993) 566
3. Sprinz J., and Helmchen G. Tetrahedron Lett. 34 (1993) 1769
4. Dawson G.J., Frost C.G., Williams J.M.J., and Coote S.J. Tetrahedron Lett. 34 (1993) 3149
5. Constantine R.N., Kim N., and Bunt R.C. Org. Lett. 5 (2003) 2279
6. Bolm C., Wenz K., and Raabe G. J. Organomet. Chem. 662 (2002) 23
7. Wiese B., Knühl G., Flubacher D., Prieß J.W., Ulriksen B., Brödner K., and Helmchen G. Eur. J. Org. Chem. (2005) 3246
8. Ogasawara M., Yoshida K., Kamei H., Kato K., Uozumi Y., and Hayashi T. Tetrahedron: Asymmetry 9 (1998) 1779
9. Gilbertson S.R., and Chang C.-W.T. Chem. Commun. (1997) 975
10. Geiser F.M., and Helmchen G. J. Org. Chem. 71 (2006) 2486
11. Shawali A.S., Elanadouli B.E., and Albar H.A. Tetrahedron 41 (1985) 1877
12. Kolb H.C., VanNieuwenhze M.S., and Sharpless K.B. Chem. Rev. 94 (1994) 2483
13. Vyskočil S., Smrčina M., Hanuš V., Polášek M., and Kočovsky P. J. Org. Chem. 63 (1998) 7738
14. Berk S.C., and Buchwald S.L. J. Org. Chem. 57 (1992) 3751
15. Coumbe T., Lawrence N.J., and Muhammad F. Tetrahedron Lett. 35 (1994) 625
16. For reviews, see:
17. Trost B.M., and Crawley M.L. Chem. Rev. 103 (2003) 2921
18. Pfaltz A., and Lautens M. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 2 (1999), Springer, Berlin Chapter 24
19. Trost B.M., and Van Vranken D.L. Chem. Rev. 96 (1996) 395
20. For recent examples of Pd-catalyzed allylic substitution, see:
21. Lussem B.J., and Gais H.-J. J. Am. Chem. Soc. 125 (2003) 6066
22. Hou X.-L., and Sun N. Org. Lett. 6 (2004) 4399
23. Lyle M.P.A., Narine A.A., and Wilson P.D. J. Org. Chem. 69 (2004) 5060
24. Mancheno O.G., Priego J., Cabrera S., Arrayas R.G., Llamas T., and Carretero J.C. J. Org. Chem. 68 (2003) 3679
25. Zhao D., and Ding K. Org. Lett. 5 (2003) 1349
26. Pàmies O., Montserrat D., and Claver C. J. Am. Chem. Soc. 127 (2005) 3646
27. Crystallographic data has been deposited in the Cambridge Crystallographic Data Centre under deposition number CCDC 292585.
28. 1H NMR (Brookhart, M.; Green, M. L. H. Prog. Inorg. Chem. 1988, 36, 1), preagostic interactions can be characterized by a downfield shift. See:
29. Roe D.M., Bailey P.M., Moseley K., and Maitlis P.M. J. Chem. Soc., Chem. Commun. (1972) 1273
30. Albinati A., Anklin C.G., Ganazzoli F., Ruegg H., and Pregosin P.S. Inorg. Chem. 26 (1987) 503
31. Albinati A., Arz C., and Pregosin P.S. Inorg. Chem. 26 (1987) 508
32. Ablinati A., Pregosin P.S., and Wombacher F. Inorg. Chem. 29 (1990) 1812
33. Yao W., Eisenstein O., and Crabtree R.H. Inorg. Chim. Acta 254 (1997) 105
34. For an excellent discussion of agostic, preagostic, and M-H hydrogen bonding, see:. Lewis J.C., Wu J., Bergman R.G., and Ellman J.A. Organometallics 24 (2005) 5737
35. Sprinz J., Kiefer M., Helmchen G., Huttner G., Walter O., and Zsolnai L. Tetrahedron Lett. 35 (1994) 1523
36. Steinhagen H., Reggelin M., and Helmchen G. Angew. Chem., Int. Ed. 36 (1997) 2108
37. Kollmar M., Goldfuss B., Reggelin M., Rominger F., and Helmchen G. Chem.-Eur. J. 7 (2001) 4913
38. Kollmar M., Steinhagen H., Janssen J.P., Goldfuss B., Malinovskaya S.A., Vázquez J., Rominger F., and Helmchen G. Chem.-Eur. J. 8 (2002) 3103
39. Brown J.M., Hulmes D.I., and Guiry P.J. Tetrahedron 50 (1994) 4493
40. Electronic differentiation of the allyl carbons was originally observed by Faller in the context of Mo complexes:
41. Faller J.K., Chao K.H., and Murray H.H. Organometallics 3 (1984) 1231
42. For related studies with P,N ligands, see:. Togni A., Burckhardt U., Gramlich V., Pregosin P.S., and Salzmann R. J. Am. Chem. Soc. 118 (1996) 1031
43. Blöchl P.E., and Togni A. Organometallics 15 (1996) 4125
44. For the effect of electronically unsymmetric diphosphines on the structure of allyl complexes, see:. Breutel C., Pregosin P.S., Salzmann R., and Togni A. J. Am. Chem. Soc. 116 (1994) 4067
45. For a general discussion, see:
46. Helmchen G., Kudis S., Sennhenn P., and Steinhagen H. Pure Appl. Chem. 69 (1997) 513
47. Helmchen G. J. Organomet. Chem. 576 (1999) 203
48. Prétôt R., Lloyd-Jones G.C., and Pfaltz A. Pure Appl. Chem. 70 (1998) 1035
49. Tsuji J., Minami I., and Shimizu I. Tetrahedron Lett. 24 (1983) 1793
50. Shimizu I., Minami I., and Tsuji J. Tetrahedron Lett. 24 (1983) 1797
51. Tsuji J., Minami I., and Shimizu I. Chem. Lett. (1983) 1325
52. Shimizu I., Takahashi K., Minami I., and Tsuji J. Tetrahedron Lett. 25 (1984) 1797
53. For asymmetric Tsuji allylation, see:
54. Behanna D.C., and Stoltz B.M. J. Am. Chem. Soc. 126 (2004) 15044
55. Trost B.M., and Xu J. J. Am. Chem. Soc. 12 (2005) 2846
56. Trost B.M., and Xu J. J. Am. Chem. Soc. 127 (2005) 17180