Stereochemistry of chiral pentacoordinate spirophosphoranes correlated with solid-state circular dichroism and 1H NMR spectroscopy

Tetrahedron Asymmetry

Volumn 20, Issue 11, 2009, Pages 1301-1307

  Hou, Jian Bo ^a   Tang, Guo ^a   Guo, Jian Nan ^a   Liu, Yan ^a   Zhang, Hui ^a   Zhao, Yu Fen ^a,b,c  

^a Key Laboratory for Chemical Biology of Fujian Province   (China)

^b XIAMEN UNIVERSITY   (China)

^c BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

LEUCINE; PHOSPHORANE DERIVATIVE; VALINE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; DIASTEREOISOMER; ENANTIOMER; GEOMETRY; ISOLATION PROCEDURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 67649661929     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.05.009     Document Type: Article

References (57)

1. For some examples, see:. Taira K., Uchimaru T., Storer J.W., Yliniemela A., Uebayashi M., and Tanabe K. J. Org. Chem. 58 (1993) 3009-3017
2. Perreault D.M., and Anslyn E.V. Angew. Chem., Int. Ed. 36 (1997) 432-450
3. Raines R.T. Chem. Rev. 98 (1998) 1045-1066
4. Takagi Y., Warashina M., Stec W.J., Yoshinari K., and Taira K. Nucleic Acids Res. 29 (2001) 1815-1834
5. For some examples, see:. Hengge A.C. Acc. Chem. Res. 35 (2002) 105-112 and references therein
6. Zhang Z.Y. Acc. Chem. Res. 36 (2003) 385-392
7. Lahiri S.D., Zhang G.F., Dunaway-Mariano D., and Allen K.N. Science 299 (2003) 2067-2071
8. Allen K.N., and Dunaway-Mariano D. Trends Biochem. Sci. 29 (2004) 495-503
9. Tremblay L.W., Zhang G.F., Dai J.Y., Dunaway-Mariano D., and Allen K.N. J. Am. Chem. Soc. 127 (2005) 5298-5299
10. Cleland W.W., and Hengge A.C. Chem. Rev. 106 (2006) 3252-3278
11. Blackburn, G. M. 17th International conference on phosphorus chemistry, Abstract Book, 2007, pp 2-3.
12. Ramirez F., and Desai N.B. J. Am. Chem. Soc. 82 (1960) 2652-2653
13. Hamilton W.C., LaPlaca S.J., and Ramirez F. J. Am. Chem. Soc. 87 (1965) 127-128
14. Hamilton W.C., LaPlaca S.J., Ramirez F., and Simth C.P. J. Am. Chem. Soc. 89 (1967) 2268-2272
15. Ramirez F. Acc. Chem. Res. 1 (1968) 168-174
16. Garrigues B., Munoz A., Koenig M., Sanchez M., and Wolf R. Tetrahedron 33 (1977) 635-643
17. Laurenco C., and Burgada R. Tetrahedron 32 (1976) 2089-2098
18. Kawashima T., Takami H., and Okazaki R. J. Am. Chem. Soc. 116 (1994) 4509-4510
19. Kawashima T., Okazaki R., and Okazaki R. Angew. Chem., Int. Ed. 36 (1997) 2500-2502
20. Kano N., Hua X.J., Kawa S., and Kawashima T. Tetrahedron Lett. 41 (2000) 5237-5241
21. Fu H., Tu G.Z., Li Z.L., Zhao Y.F., and Zhang R.Q. J. Chem. Soc., Perkin Trans. 1 (1997) 2021-2022
22. Lu H.Y., Zhang N.J., and Zhao Y.F. Chin. Chem. Lett. 8 (1997) 397-400
23. Yu L., Liu Z., Fang H., and Zhao Y.F. Acta Crystallogr., Sect. E 61 (2005) o261-o262
24. Yu L., Liu Z., Fang H., Zeng Q.L., and Zhao Y.F. Amino Acid 28 (2005) 369-372
25. Cao S.X., Liu J.M., Xie Y.L., Liao X.C., and Zhao Y.F. Acta Crystallogr., Sect. E 62 (2006) o4642-o4643
26. Timosheva N.V., Chandrasekaran A., and Holmes R.R. J. Am. Chem. Soc. 127 (2005) 12474-12475
27. Timosheva N.V., Chandrasekaran A., and Holmes R.R. Inorg. Chem. 45 (2006) 3113-3123
28. Timosheva N.V., Chandrasekaran A., and Holmes R.R. Inorg. Chem. 45 (2006) 10836-10848
29. Berry R.S. J. Chem. Phys. 32 (1960) 933-938
30. Westheimer F.H. Acc. Chem. Res. 1 (1968) 70-78
31. Klaebe A., Brazier J.F., Carrelhas A.C., Garrigues B., Marre M.R., and Contreras R. Tetrahedron 38 (1982) 2111-2122
32. Uchimaru T., Uebayashi M., Hirose T., Tsuzuki S., Yliniemela A., Tanabe K., and Taira K. J. Org. Chem. 61 (1996) 1599-1608
33. Kojima S., Nakamoto M., and Akiba K.-Y. Eur. J. Org. Chem. (2008) 1715-1722
34. Trippett S. Phosphorus and Sulfur 1 (1976) 89-98
35. Brierley J., Trippett S., and White M.W. J. Chem. Soc., Perkin Trans. 1 (1977) 273-278
36. Holmes R.R. Pentacoordinated Phosphorus-Structure and Spectroscopy. ACS Monograph Series 175 and 176 Vols. I, II (1980), American Chemical Society, Washington, DC
37. Nakamoto M., Kojima S., Matsukawa S., Yamamoto Y., and Akiba K.-Y. J. Organomet. Chem. 643-644 (2002) 441-452
38. Matsukawa S., Kajiyama K., Kojima S., Furuta S.Y., Yamamoto Y., and Akiba K.-Y. Angew. Chem., Int. Ed. 41 (2002) 4718-4722
39. Kumara Swamy K.C., and Satish Kumar N. Acc. Chem. Res. 39 (2006) 324-333
40. Kojima S., Kajiyama K., Nakamoto M., and Akiba K.-Y. J. Am. Chem. Soc. 118 (1996) 12866-12867
41. Matsukawa S., Kojima S., Kajiyama K., Yamamoto Y., Akiba K.-Y., Re S., and Nagase S. J. Am. Chem. Soc. 124 (2002) 13154-13170
42. Kajiyama K., Yoshimune M., Kojima S., and Akiba K.-Y. Eur. J. Org. Chem. (2006) 2739-2746
43. Jiang X.D., Matsukawa S., Yamamichi H., Kakuda K., Kojima S., and Yamamoto Y. Eur. J. Org. Chem. (2008) 1392-1405
44. Garrigues B., Klaebe A., and Munoz A. Phosphorus and Sulfur 8 (1980) 153-156
45. Klaebe A., Brazier J.F., Garrigues B., and Wolf R. Phosphorus and Sulfur 10 (1981) 53-59
46. Fu H., Xu J.H., Wang R.J., Chen Z.Z., Tu G.Z., Wang Q.Z., and Zhao Y.F. Phosphorus, Sulfur, Silicon 178 (2003) 1963-1971
47. Kojima S., Kajayama K., and Akiba K.-Y. Tetrahedron Lett. 35 (1994) 7037-7040
48. Kojima S., Kajiyama K., and Akiba K.-Y. Bull. Chem. Soc. Jpn. 68 (1995) 1785-1797
49. Kojima S., Kawaguchi K., Matsukawa S., and Akiba K.-Y. Tetrahedron 59 (2003) 255-265
50. Kuroda R. Solid-State CD: Application to Inorganic and Organic Chemistry. In: Berova N., Nakanishi K., and Woody R.W. (Eds). Circular Dichroism: Principles and Applications. 2nd ed. (2000), John Wiley & Sons 159
51. Kuroda R., and Honma T. Chirality 12 (2000) 269-277
52. Wang Y.J., Luo G.G., Yu Y., Lin L.R., Zhang H., Huang R.B., and Zheng L.S. Chin. J. Org. Chem. 28 (2008) 903-906
53. Bilotti I., Biscraini P., Castiglioni E., Ferranti F., and Kuroda R. Chirality 14 (2002) 750-756
54. von Zelewsky A. Stereochemistry of Coordination Compounds (1996), John Wiley & Sons Ltd, Chichester pp 100-101
55. Mamula O., Von Zelewsky A., Bark T., Stoeckli-Evans H., Neels A., and Bernardinelli G. Chem. Eur. J. 6 (2000) 3575-3585
56. Sheldrick G.M. Acta Crystallogr., Sect. A 46 (1990) 467
57. Sheldrick, G. M. shelxl-97, Program for Crystal Structure Refinement from Diffraction Data, University of Göttingen: Germany, 1997.