Sterically congested "roofed" 2-iminothioethers as new chiral ligands for palladium-catalyzed asymmetric allylic alkylation

Heterocycles

Volumn 66, Issue 1, 2005, Pages 135-141

  Tokuda, Ryoh ^a   Matsunaga, Hirofumi ^a   Ishizuka, Tadao ^a   Nakajima, Makoto ^a   Kunieda, Takehisa ^b  

^a KUMAMOTO UNIVERSITY   (Japan)

^b SOJO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646865929     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-S(K)50     Document Type: Article

References (56)

1. For reviews, see:. In: Ojima I. (Ed). 'Catalytic Asymmetric Synthesis' (1993), VCH, New York
2. Jacobsen E.N., Pfaltz A., and Yamamoto H. 'Comprehensive Asymmetric Catalysis' (1999), Springer, New York
3. Selected papers:. Müller D., Umbricht G., Weber B., and Pfaltz A. Helv. Chim. Acta 74 (1991) 232
4. Evans D.A., Woerpel K.A., Hinman M.M., and Faul M.M. J. Am. Chem. Soc. 113 (1991) 726
5. Corey E.J., Imai N., and Zhang H.-Y. J. Am. Chem. Soc. 113 (1991) 728
6. Ghosh A.K., Mathivanan P., and Cappiello J. Tetrahedron: Asymmetry 9 (1998) 1
7. McManus H.A., and Guiry P.J. Chem. Rev. 104 (2004) 4151
8. Selected papers:. Kagan H.B., and Dang T.-P. J. Am. Chem. Soc. 94 (1972) 6429
9. Hayashi T., Yamamoto A., Ito Y., Nishioka E., Miura H., and Yanagi K. J. Am. Chem. Soc. 111 (1989) 6301
10. Noyori R., and Takaya H. Acc. Chem. Res. 23 (1990) 345
11. Sawamura M., and Ito Y. Chem. Rev. 92 (1992) 857
12. Trost B.M., and Vranken D.L.V. Chem. Rev. 96 (1996) 395
13. Matt P.v., and Pfaltz A. Angew. Chem., Int. Ed. Engl. 32 (1993) 566
14. Sprinz J., and Helmchen G. Tetrahedron Lett. 34 (1993) 1769
15. Dawson G.J., Frost C.G., Williams J.M.J., and Coote S.J. Tetrahedron Lett. 34 (1993) 3149
16. Helmchen G., and Pfaltz A. Acc. Chem. Res. 33 (2000) 336
17. Guiry P.J., and Saunders C.P. Adv. Synth. Catal. 346 (2004) 497
18. Chensney A., Bryce M.R., Chubb R.W.J., Batsanov A.S., and Howard J.A.K. Tetrahedron: Asymmetry 8 (1997) 2337
19. Boog-Wick K., Pregosin P.S., and Trabesinger G. Organometallics 17 (1998) 3254
20. Imai Y., Zhang W., Kida T., Nakatsuji Y., and Ikeda I. Synlett 1319 (1999)
21. Park J., Quan Z., Lee S., Ahn K.H., and Cho C.-W. J. Organomet. Chem. 584 (1999) 140
22. Christoffers J., Mann A., and Pickardt J. Tetrahedron 55 (1999) 5377
23. Hou X.-L., Wu X.-W., Dai L.-X., Cao B.-X., and Sun J. Chem. Commun. (2000) 1195
24. You S.-L., Hou X.-L., Dai L.-X., Yu Y.-H., and Xia W. J. Org. Chem. 67 (2002) 4684
25. Gómez M., Jansat S., Muller G., Maestro M.A., and Mahía J. Organometallics 21 (2002) 1077
26. Chelucci G., and Cabras M.A. Tetrahedron: Asymmetry 7 (1996) 965
27. Vries A.H.M.d., Hof R.P., Staal D., Kellogg R.M., and Feringa B.L. Tetrahedron: Asymmetry 8 (1997) 1539
28. Koning B., Meetsma A., and Kellogg R.M. J. Org. Chem. 63 (1998) 5533
29. Chelucci G., Culeddu N., Saba A., and Valenti R. Tetrahedron: Asymmetry 10 (1999) 3537
30. Chelucci G., Bacchi A., Fabbri D., Saba A., and Ulgheri F. Tetrahedron Lett. 40 (1999) 553
31. Adams H., Anderson J.C., Cubbon R., James D.S., and Mathias J.P. J. Org. Chem. 64 (1999) 8256
32. Rassias G.A., Page P.C.B., Reignier S., and Christie S.D.R. Synlett (2000) 379
33. Petra D.G.I., Kamer P.C.J., Spek A.L., Schoemaker H.E., and Leeuwen P.W.N.M.v. J. Org. Chem. 65 (2000) 3010
34. Braga A.L., Paixão M.W., Milani P., Silveira C.C., Rodrigues O.E.D., and Alves E.F. Synlett (2004) 1297
35. Schneider P.H., Schrekker H.S., Silveira C.C., Wessjohann L.A., and Braga A.L. Eur. J. Org. Chem. (2004) 2715
36. Hoshimoto S., Matsunaga H., and Kunieda T. Chem. Pharm. Bull. 48 (2000) 1541
37. 30NS 484.2099, found 484.2188.
38. For reviews, see:. Frost C.G., Howarth J., and Williams J.M.J. Tetrahedron: Asymmetry 3 (1992) 1089
39. For recent reports, see:. Tietze L.F., Ila H., and Bell H.P. Chem. Rev. 104 (2004) 3453
40. Pàmies O., Diéguez M., and Claver C. J. Am. Chem. Soc. 127 (2005) 3646
41. Faller J.W., and Wilt J.C. Org. Lett. 7 (2005) 633
42. Chelucci G., and Orrù G. Tetrahedron Lett. 46 (2005) 3493
43. Anderson J.C., and Osborne J. Tetrahedron: Asymmetry 16 (2005) 931
44. Braga A.L., Sehnem J.A., Lüdtke D.S., Zeni G., Silveira C.C., and Marchi M.I. Synlett (2005) 1331
45. Diéguez M., Pàmies O., and Claver C. J. Org. Chem. 70 (2005) 3363
46. Ferioli F., Fiorelli C., Martelli G., Monari M., Savoia D., and Tobaldin P. Eur. J. Org. Chem. (2005) 1416
47. Guimet E., Diéguez M., Ruiz A., and Claver C. Tetrahedron: Asymmetry 16 (2005) 959
48. Bueno A., Moreno R.M., and Moyano A. Tetrahedron: Asymmetry 16 (2005) 1763
49. 3 effected asymmetric induction to give higher ee than NaH. Trost B.M., Krueger A.C., Bunt R.C., Zambrano J. J. Am. Chem. Soc. 118 (1996) 6520
50. 3 as rate-acceleration is ongoing. Trost B.M., and Vranken D.L.V. Chem. Rev. 96 (1996) 395
51. Cotton F.A., Wilkinson G., Murillo C.A., and Bochmann M. 'Survey of Transition Metal Chemistry'. sixth edition. Advanced Inorganic Chemistry (1999), Wiley-Interscience Publication, New York 633-691 Chapter 16
52. Other reports indicating that the sulfur atom is a better π-acceptor than a nitrogen atom:. HuHeey J. Inorganic Chemistry (1983), Harper and Row, New York
53. Sprinz J., Kiefer M., Helmchen G., Reggelin M., Huttner G., Walter O., and Zsolnai L. Tetrahedron Lett. 35 (1994) 1523
54. Allen J.V., Coote S.J., Dawson G.J., Frost C.G., Martin C.J., and Williams J.M.J. J. Chem. Soc., Perkin Trans. l (1994) 2065
55. Chesney A., and Bryce M.R. Tetrahedron: Asymmetry 7 (1996) 3247
56. Morimoto T., Tachibana K., and Achiwa K. Synlett (1977) 783