Amino acid-derived lodobenzene dicarboxylates: Reagents for oxidative conversion of alkenes to amino acid esters

Organic Letters

Volumn 6, Issue 20, 2004, Pages 3613-3615

  Koposov, Alexey Y ^a   Boyarskikh, Vyacheslav V ^a   Zhdankin, Viktor V ^a  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AMINO ACID DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; ESTER; IODIDE; ALKENE; AMINO ACID; DICARBOXYLIC ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IODOBENZENE;

ARTICLE; CARBOXYLATION; CHEMICAL MODIFICATION; OXIDATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALKENES; AMINO ACIDS; CATALYSIS; DICARBOXYLIC ACIDS; ESTERS; INDICATORS AND REAGENTS; IODOBENZENES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 6444241594     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0484714     Document Type: Article

References (24)

1. (a) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997.
2. (b) Togo, H.; Katohgi, M. Synlett 2001, 565.
3. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
4. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
5. (a) Kirschning, A.; Plumeier, C.; Rose, L. J. Chem. Soc., Chem. Commun. 1998, 33.
6. (b) Hashem, A.; Jung, A.; Ries, M.; Kirschning, A. Synlett 1998, 195.
7. (c) Tingoli, M.; Tiecco, M.; Testaferri, L.; Temperini, A. Synth. Commun. 1998, 28, 1769.
8. (a) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826.
9. (b) Merkushev, E. B.; Novikov, A. N.; Makarchenko, S. S.; Moskal'chuk, A. S.; Glushkova, V. V.; Kogai, T. I.; Polyakova, L. G. J. Org. Chem. USSR (Engl. Trans.) 1975, 11, 1246.
10. (c) Stang, P. J.; Boehshar, M.; Wingert, H.; Kitamura, T. J. Am. Chem. Soc. 1988, 110, 3272.
11. (d) Imamoto, T.; Koto, H. Chem. Lett. 1986, 967.
12. (e) Hatzigrigoriou, E.; Varvoglis, A.; Bakola-Christianopoulou, M. J. Org. Chem. 1990, 55, 315.
13. (f) Ray, D. G., III; Koser, G. F. J. Am. Chem. Soc. 1990, 112, 5672.
14. (g) Ochiai, M.; Takaoka, Y.; Masaki, Y.; Nagao, Y.; Shiro, M. J. Am. Chem. Soc. 1990, 112, 5677.
15. Ray, D. G.; Koser, G. F. J. Org. Chem. 1992, 57, 1607.
16. No reaction was observed between unprotected amino acids and DIB due to the insolubility of amino acids in organic solvents. Protected amino acids 2 are commercially available or can be prepared by known methods; see: Zhdankin, V. V.; Smart, J. T.; Zhao, P.; Kiprof, P. Tetrahedron Lett. 2000, 41, 5299.
17. +.
18. +.
19. 2, all data). Full details on the crystal structure of 4c are available in Supporting Information.
20. (a) Prevost, C. Compt. Rend. 1933, 196, 1129.
21. (b) Woodward, R. B.; Brutcher, F. V. J. Am. Chem. Soc. 1958, 80, 209.
22. (c) Brimble, M. A.; Nairn, M. R. J. Org. Chem. 1996, 61, 4801.
23. (d) Whitesell, J. K.; Minton, M. A. J. Am. Chem. Soc. 1987, 109, 6403.
24. (e) Kim, J. H.; Long, M. J. C.; Kim, J. Y.; Park, K. H. Org. Lett. 2004, 6, 2273.