A new dinuclear chiral salen complexes for asymmetric ring opening and closing reactions: Synthesis of valuable chiral intermediates

Journal of Organometallic Chemistry

Volumn 691, Issue 9, 2006, Pages 1862-1872

  Thakur, Santosh Singh ^a   Chen, Shu Wei ^a   Li, Wenji ^a   Shin, Chang Kyo ^a   Kim, Seong Jin ^b   Koo, Yoon Mo ^a   Kim, Geon Joong ^a,b  

^a Inha University   (South Korea)

^b RStech Corp #305 Venture Town   (South Korea)

Author keywords

Asymmetric catalysis; Asymmetric ring opening reactions; Chiral dinuclear catalyst; Chiral intermediates; Kinetic resolution

Indexed keywords

CARBOXYLIC ACIDS; CATALYST ACTIVITY; CHLORIDE MINERALS; SYNTHESIS (CHEMICAL);

ASYMMETRIC CATALYSIS; ASYMMETRIC RING OPENING REACTIONS; CHIRAL DINUCLEAR CATALYST; CHIRAL INTERMEDIATES;

COMPLEXATION;

EID: 33645455679     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.12.044     Document Type: Article

References (61)

1. I. Ojima Catalytic Asymmetric Synthesis second ed. 2000 Wiley-VCH New York
2. E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis vols. I-III 1999 Springer Heidelberg
3. M. Shibasaki, M. Kanai, and K. Funabashi Chem. Commun. 2002 1989
4. M. Shibasaki, and N. Yoshikawa Chem. Rev. 102 2002 2187
5. T. Iida, N. Yamamoto, S. Matsunaga, H.-G. Woo, and M. Shibasaki Angew. Chem. Int. Ed. 37 1998 2223
6. S. Matsunaga, T. Yoshida, H. Morimoto, N. Kumagai, and M. Shibasaki J. Am. Chem. Soc. 126 2004 8777
7. B.M. Trost, and V.S.C. Yeh Angew. Chem. 114 2002 889
8. Angew. Chem. Int. Ed. 41 2002 861 and references therein
9. B.M. Trost, and T. Mino J. Am. Chem. Soc. 125 2003 2410
10. B.M. Trost, and L.R. Terrell J. Am. Chem. Soc. 125 2003 338
11. Yu.N. Belokon, M. North, V.I. Maleev, N.V. Voskoboev, M.A. Moskalenko, A.S. Peregudov, A.V. Dmitriev, N.S. Ikonnikov, and H.B. Kagan Angew. Chem. Int. Ed. 43 2004 4085
12. S. Kobayashi, K. Arai, H. Shimizu, Y. Ihori, H. Ishitani, and Y. Yamashita Angew. Chem. Int. Ed. 44 2005 761
13. M. Yang, C. Zhu, F. Yuan, Y. Huang, and Y. Pan Org. Lett. 7 2005 1927
14. H.C. Kolb, M.S. Van Nieuwenhze, and K.B. Sharpless Chem. Rev. 94 1994 2483
15. L.P.C. Nielson, C.P. Stevenson, D.G. Backmond, and E.N. Jacobsen J. Am. Chem. Soc. 126 2004 1360
16. S.K. Kim, and E.N. Jacobsen Angew. Chem. Int. Ed. 43 2004 3952
17. J.F. Larrow, and E.N. Jacobsen Top. Organomet. Chem. 6 2004 123 and references cited therein
18. S. Aertsa, A. Buekenhoudta, H. Weytena, I.F.J. Vankelecom, and P.A. Jacobs Tetrahedron: Asymmetry 16 2005 657
19. L. Aouni, K.E. Hemberger, S. Jasmin, H. Kabir, J.F. Larrow, I. Le-Fur, P. Morel, and T. Schlama H.U. Blaser E. Schidmt Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions 2004 Wiley-VCH Verlag Gmbh & Co. KgaA Weinheim, Germany 165
20. J.F. Larrow, K.E. Hemberger, S. Jasmin, H. Kabir, and P. Morel Tetrahedron: Asymmetry 14 2003 3589
21. M. Tokunaga, J.F. Larrow, F. Kakiuchi, and E.N. Jacobsen Science 277 1997 936
22. M.E. Furrow, S.E. Schaus, and E.N. Jacobsen J. Org. Chem. 63 1998 6776
23. T. Katsuki E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis 1999 Springer New York (Chapters 18.1 and 35)
24. B.E. Rossiter J.D. Morrison Asymmetric Synthesis vol. 5 1985 Academic Press New York (Chapter 7)
25. R.A. Johnson, and K.B. Sharpless I. Ojima Catalytic Asymmetric Synthesis second ed. 2000 Wiley-VCH New York (Chapter 6A)
26. T. Katsuki, and V.S. Martin Org. React. 48 1996 1
27. J.M. Ready, and E.N. Jacobsen J. Am. Chem. Soc. 123 2001 2687
28. J.M. Ready, and E.N. Jacobsen Angew. Chem. Int. Ed. 41 2002 1374
29. D.E. White, and E.N. Jacobsen Tetrahedron: Asymmetry 14 2003 3633
30. S.S. Thakur, W. Li, S.J. Kim, and G.-J. Kim Tetrahedron Lett. 46 2005 2263
31. C.K. Shin, S.J. Kim, and G.-J. Kim Tetrahedron Lett. 45 2004 7429
32. G.-J. Kim, H. Lee, and S.J. Kim Tetrahedron Lett. 44 2003 5005
33. S.S. Thakur, W. Li, C.K. Shin, and G.-J. Kim Catal. Lett. 104 2005 151
34. D.W. Park, S.D. Choi, C.Y. Lee, and G.-J. Kim Catal. Lett. 78 2002 145
35. D. Atwood, and M.J. Harvey Chem. Rev. 101 2001 37 and references cited therein
36. D. Atwood, and P. Wei Chem. Commun. 1997 1427
37. E. Solari, F. Corazza, C. Floriani, A. Chiesi-Villa, and C. Guastini J. Chem. Soc., Dalton Trans. 1990 1345
38. S.J. Gruber, C.M. Harris, and E. Sinn Inorg. Chem. 2 1968 268
39. R.H. Holm, W. Everett, and A. Chakravorty Prog. Inorg. Chem. 7 1966 83
40. H. Aoi, M. Ishimori, and T. Tsuruta Bull. Chem. Soc. Jpn. 48 1975 1897
41. D.A. Annis, and E.N. Jacobsen J. Am. Chem. Soc. 121 1999 4147
42. K.M. Spencer, S.J. Cianciosi, J.E. Baldwin, T.B. Freedman, and L.A. Nafie Appl. Spectrosc. 44 1990 235
43. For review see: T.B. Freedman, X. Cao, R.K. Dukor, and L.A. Nafie Chirality 15 2003 743
44. R.G. Konsler, J. Karl, and E.N. Jacobsen J. Am. Chem. Soc. 120 1998 10780
45. R. Breinbauer, and E.N. Jacobsen Angew. Chem. Int. Ed. 39 2000 3604
46. 2O as Lewis acid, see: B.C. Ranu Eur. J. Org. Chem. 2000 2347
47. S. Sengupta, and S. Mondal Tetrahedron Lett. 40 1999 8685
48. S. Uemura, K. Sohma, and M. Okano Bull. Chem. Soc. Jpn. 45 1972 860
49. C. Bonini, and G. Righi Synthesis 1994 225
50. Halohydrins also serve as important synthetic intermediates in their own right and are critical subunits for the synthesis of halogenated marine natural products. For reviews see: W. Fenical P.J. Scheuer Marine Natural Products vol. 2 1980 Academic Press New York 174
51. N.N. Joshi, M. Srebnik, and H.C. Brown J. Am. Chem. Soc. 110 1988 6246
52. Y. Naruse, T. Esaki, and H. Yamamoto Tetrahedron 44 1988 4747
53. C.E. Garrett, and G.C. Fu J. Org. Chem. 62 1997 4534
54. S.E. Denmark, and P.A. Barsanti J. Org. Chem. 63 1988 2428
55. L.S. Wang, and T.K. Hollis Org. Lett. 5 2003 2543
56. T. Takeichi, M. Arihara, M. Ishimori, and T. Tsuruta Tetrahedron 36 1980 3391
57. E.N. Jacobsen, F. Kakiuchi, R.G. Konsler, J.F. Larrow, and M. Tokunaga Tetrahedron Lett. 38 1997 773
58. M. Carron, and K.B. Sharpless J. Org. Chem. 50 1985 1560
59. G.H. Posner Angew. Chem., Int. Ed. Engl. 17 1978 487
60. S. Brickner, D. Hutchinson, M. Barbachyn, P. Manninen, D. Ulanowicz, S. Garmon, K. Grega, S. Hendges, D. Toops, C. Ford, and G. Zurenko J. Med. Chem. 39 1996 673
61. M.A. Weidner-Wells, C.M. Boggs, B.D. Foleno, J. Melton, K. Bush, R.M. Goldschmidt, and D.J. Hlasta Bioorg. Med. Chem. 10 2002 2345