Efficient catalyst turnover in the phosphitylation of alcohols with phosphoramidites

Tetrahedron Letters

Volumn 50, Issue 9, 2009, Pages 975-978

  Brady, Patrick B ^a   Morris, Elizabeth M ^a   Fenton, Owen S ^a   Sculimbrene, Bianca R ^a  

^a Department of Biology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; ISOCYANIC ACID DERIVATIVE; PHOSPHORAMIDOUS ACID DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; CHEMICAL REACTION; PHOSPHITYLATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 58149501807     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.12.065     Document Type: Article

References (43)

1. Baker W.R., Cai S., Dimitroff M., Fang L., Huh K.K., Ryckman D.R., Shang X., Shawar R.M., and Therrien J.H. J. Med. Chem. 47 (2004) 4693
2. Saulnier M.G., Langley D.R., Kadow J.F., Senter P.D., O Knipe J., Tun M.M., Vyas D.M., and Doyle T.W. Bioorg. Med. Chem. Lett. 4 (1994) 2567
3. Jones S., and Selitsianos D. Org. Lett. 4 (2002) 3671
4. Sculimbrene B.R., and Miller S.J. J. Am. Chem. Soc. 123 (2001) 10125
5. Deutsch A., and Ferno O. Nature 156 (1945) 604
6. Atherton F.R., Openshaw H.T., and Todd A.R. J. Chem. Soc. (1945) 382
7. Nelson T.D., Rosen J.D., Bhupathy M., McNamara J., Sowa M.J., Rush C., and Crocker L.S. Org. Synth. 80 (2003) 219
8. Dudek G.O., and Westheimer F.H. J. Chem Soc. (1959) 2641
9. Nifantiev E.E., Grachev M.K., and Burmistrov S.Y. Chem. Rev. 100 (2000) 3755 and references therein
10. Watanabe Y., Maehara S., and Ozaki S. J. Chem Soc., Perkin Trans. 1 (1992) 1879
11. Martin S.F., and Josey J.A. Tetrahedron Lett. 29 (1988) 3631
12. Hayakawa Y., Hyodo M., Kimura K., and Kataoka M. Chem. Commun. (2003) 1704
13. 2O:. Letsinger R.L., and Lunsford W.B. J. Am. Chem. Soc. 98 (1976) 3655
14. mCPBA:. Ogilvie K.K., and Nemer M.J. Tetrahedron Lett. 22 (1981) 2531
15. Dioxiranes:. Kataoka M., Hattori A., Okino S., Hyodo M., Asano M., Kawai R., and Hayakawa Y. Org. Lett. 6 (2001) 815 and references therein
16. Singlet oxygen:. Boldue P.R., and Goe G.L. J. Org. Chem. 21 (1974) 3178
17. Alkyl peroxides:. Hayakawa Y., Uchiyama M., and Noyori R. Tetrahedron Lett. 27 (1986) 4191
18. This is due to nucleophilic attack on carbon instead of phosphorous, see:. Modro T.A., and Moorhoff C.M. J. Phys. Org. Chem. 2 (1989) 263
19. Zervas L., and Dilaris I. J. Chem. Soc. 77 (1954) 5354
20. Beaucage S.L., and Iyer R.P. Tetrahedron 48 (1992) 2223
21. For other catalysts see:. Hayakawa Y., Iwase T., Nurminen E.J., Tsukamoto M., and Kataoka M. Tetrahedron Lett. 61 (2005) 2203
22. Hayakawa Y., Kawai R., Hirata A., Sugimoto J., Kataoka M., Sakakura A., Hirose M., and Noyori R. J. Am. Chem. Soc. 123 (2001) 8165
23. Eicher T., and Hauptmann S. The Chemistry of Heterocycles. 2nd ed. (2003), Wiley-VCH, Weinheim, Germany
24. Hayakawa Y., and Kataoka M. J. Am. Chem. Soc. 119 (1997) 11758
25. Booth R.J., and Hodges J.C. J. Am. Chem. Soc. 119 (1997) 4882
26. Cho J.K., White P.D., Klute W., Dean T.W., and Bradley M. Chem. Commun. (2004) 502
27. Linclau B., Sing A.K., and Curran D.P. J. Org. Chem. 64 (1999) 2835
28. + requires m/z 361.1569. Found 361.1536 (FAB).
29. From NMR analysis, product decomposed slowly on the column to styrene and dibenzylphosphate.
30. Graham S.M., and Pope S.C. Org. Lett. 5 (1999) 733
31. Watanabe Y., Munetsugu H., and Hayashi M. Chem. Lett. (2002) 292
32. Manoharan M., Lu Y., Casper M.D., and Just G. Org. Lett. 2 (2000) 243
33. For synthesis of 4 from diisopropylphosphoramidous dichloride see:. Arslan T., Mamaev S.V., Mamaeva N.V., and Hecht S.M. J. Am. Chem. Soc. 119 (1997) 10877
34. For protein examples, see:. Vogel E.M., and Imperiali B. Protein Sci. 16 (2007) 550
35. Hahn M.E., and Muir T.W. Angew. Chem., Int. Ed. 43 (2004) 5800
36. For small molecule examples, see:. Dinkel C., and Schultz C. Tetrahedron Lett. 44 (2003) 1157
37. Marriott G. Caged Compounds. Methods in Enzymology Vol. 291 (1998), Academic Press, New York
38. Scheuer-Larsen C., Dahl B.M., Wengel J., and Dahl O. Tetrahedron Lett. 39 (1998) 8361
39. Christov V.C., and Ivanova J.G. Synth. Commun. 36 (2006) 2231
40. Macomber R.S., and Krudy G.A. J. Org. Chem. 48 (1983) 1425 and references therein
41. Yu F., Lian X., and Ma S. Org. Lett. 9 (2007) 1703
42. Chakravarty M., and Swamy K.C.K. J. Org. Chem. 71 (2006) 9128
43. Guo H., Zheng Z., Yu F., Ma S., Holuigue A., Tromp D.S., Elsevier C.J., and Yu Y. Angew. Chem., Int. Ed. 45 (2006) 4997