Synthesis and oxidative reactivity of new chiral hypervalent iodine(V) reagents based on (S)-proline

Tetrahedron Letters

Volumn 47, Issue 35, 2006, Pages 6301-6304

  Ladziata, Uladzimir ^a   Carlson, Jeffrey ^a   Zhdankin, Viktor V ^a  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALCOHOL DERIVATIVE; IODINE; OXAZINE DERIVATIVE; OXIDIZING AGENT; PROLINE; REAGENT; SULFIDE;

ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; OXIDATION; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 33746300304     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.103     Document Type: Article

References (43)

1. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155
2. Frigerio M., and Santagostino M. Tetrahedron Lett. 35 (1994) 8019
3. Thottumkara A.P., and Vinod T.K. Tetrahedron Lett. 43 (2002) 569
4. Dess D.B., and Martin J.C. J. Org. Chem. 113 (1991) 7277
5. Stickley S.H., and Martin J.C. Tetrahedron Lett. 36 (1995) 9117
6. Macikenas D., Skrzypczak-Jankun E., and Protasiewicz J.D. Angew. Chem., Int. Ed. Engl. 39 (2000) 2007
7. Meprathu B.V., Justik M.W., and Protasiewicz J.D. Tetrahedron Lett. 46 (2005) 5187
8. Zhdankin V.V., Koposov A.Y., Netzel B.C., Yashin N.V., Rempel B.P., Ferguson M.J., and Tykwinski R.R. Angew. Chem., Int. Ed. 42 (2003) 2194
9. Zhdankin V.V., Litvinov D.N., Koposov A.Y., Ferguson M.J., McDonald R., and Tykwinski R.R. J. Chem. Soc., Chem. Commun. (2004) 106
10. Zhdankin V.V., Koposov A.Y., Litvinov D.N., Ferguson M.J., McDonald R., Luu T., and Tikwinski R.R. J. Org. Chem. 70 (2005) 6484
11. Koposov A.Y., and Zhdankin V.V. Synthesis (2005) 22
12. In: Wirth T. (Ed). Hypervalent Iodine Chemistry (2003), Springer, Berlin
13. Ochiai M. In: Akiba K. (Ed). Chemistry of Hypervalent Compounds (1999), VCH, New York
14. Tohma H., and Kita Y. Adv. Synth. Catal. 346 (2004) 111
15. Wirth T. Angew. Chem., Int. Ed. 44 (2005) 3656
16. Zhdankin V.V., and Stang P.J. Chem. Rev. 102 (2002) 2523
17. Zhdankin V.V. Curr. Org. Synth. 2 (2005) 121
18. Ladziata U., and Zhdankin V.V. ARKIVOC (2006) 26
19. Fan Q.-H., Li Y.-M., and Chan A.S.C. Chem. Rev. 102 (2002) 3385
20. Fu G.C. Acc. Chem. Res. 33 (2000) 412
21. Johnson J.S., and Evans D.A. Acc. Chem. Res. 33 (2000) 325
22. Hatzigrigoriou E., Varvoglis A., and Bakola-Christianopoulou M. J. Org. Chem. 55 (1990) 315
23. Ray D.G., and Koser G.F. J. Am. Chem. Soc. 112 (1990) 5672
24. Ochiai M., Takaoka Y., Masaki Y., Nagao Y., and Shiro M. J. Am. Chem. Soc. 112 (1990) 5677
25. Ray D.G., and Koser G.F. J. Org. Chem. 57 (1992) 1607
26. Rabah G.A., and Koser G.F. Tetrahedron Lett. 37 (1996) 6453
27. Kitamura T., Lee C.H., Taniguchi Y., Fujiwara Y., Matsumoto M., and Sano Y. J. Am. Chem. Soc. 119 (1997) 619
28. Ochiai M., Kitagawa Y., Takayama N., Takaoka Y., and Shiro M. J. Am. Chem. Soc. 121 (1999) 9233
29. Wirth T., and Hirt U.H. Tetrahedron: Asymmetry 8 (1997) 23
30. Hirt U.H., Spingler B., and Wirth T. J. Org. Chem. 63 (1998) 7674
31. Hirt U.H., Schuster M.F.H., French A.N., Wiest O.G., and Wirth T. Eur. J. Org. Chem. (2001) 1569
32. Tohma H., Takizawa S., Watanabe H., Fukuoka Y., Maegawa T., and Kita Y. J. Org. Chem. 64 (1999) 3519
33. Tohma H., Takizawa S., Morioka H., Maegawa T., and Kita Y. Chem. Pharm. Bull. 48 (2000) 445
34. Ladziata U., Koposov A.Y., Lo K.Y., Willging J., Nemykin V.N., and Zhdankin V.V. Angew. Chem., Int. Ed. 44 (2005) 7127
35. Ladziata U., Willging J., and Zhdankin V.V. Org. Lett. 8 (2006) 167
36. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138
37. Han Z., Wang R., Zhou Y., and Liu L. Eur. J. Org. Chem. (2005) 934
38. Neises B., and Steglich W. Angew. Chem., Int. Ed. 17 (1978) 522
39. +.
40. 3) to give the product. Optical rotation of the obtained sample was determined and the % ee was calculated.
41. 25 +41.2 (c 0.5, EtOH; 95% ee (R)). Matharu D.S., Morris D.J., Kawamoto A.M., Clarkson G.J., and Willsa M. Org. Lett. 24 (2005) 5489
42. 25 -65 (c 1.0, MeOH; 40% ee (R)). Pesch J., Harms K., and Bach T. Eur. J. Org. Chem. (2004) 2025
43. 25 +151 (c 1.2, EtOH; 100% ee (R)). Puchot C., Samuel O., Duach E., Zhao S., Agami C., and Kagan H.B. J . Am. Chem. Soc. 108 (1986) 2353