2,2-Bis(ethoxycarbonyl)vinyl (BECV) as a versatile amine protecting group for selective functional-group transformations

Chemistry - A European Journal

Volumn 16, Issue 9, 2010, Pages 2938-2943

  Ilangovan, Andivelu ^a   Kumar, Rajendran Ganesh ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

Author keywords

Amines; Amino acids; Deprotection; Functional group transformations; Protecting groups

Indexed keywords

ALIPHATIC ESTERS; DEPROTECTION; ETHYLENE DIAMINE; FUNCTIONAL GROUP TRANSFORMATIONS; GROUP TRANSFORMATIONS; N-ALKYLATION; PROTECTING GROUP; PROTECTING GROUPS; ROOM TEMPERATURE; SELECTIVE DEPROTECTION; SELECTIVE PROTECTION;

ACYLATION; ALKYLATION; AMIDES; AMINES; AMINO ACIDS; ESTERIFICATION; ESTERS; ETHERS; FUNCTIONAL GROUPS; ORGANIC ACIDS;

AMINATION;

EID: 77149128643     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902054     Document Type: Article

References (25)

1. S. Pothukanuri, N. Winssinger, Org. Lett. 2007, 9, 2223-2225.
2. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1999, pp. 518-525; T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1999, pp. 736-739.
3. M. Wakselman, "Di-tert-butyl dicarbonate" in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. Paquette), Wiley, New York, 2004.
4. B. W. Bycroft, W. C. Chan, S. R. Chhabra, N. D. Hone, J. Chem. Soc. Chem. Commun. 1993, 778-779.
5. S. R. Chhabra, B Hothi, D. J. Evans, P. D. White, B. W. Bycroft, W. C. Chan, Tetrahedron Lett. 1998, 39, 1603-1606.
6. J. J. Díaz-Mochón, L. Bialy, M. Bradley, Org. Lett. 2004, 6, 1127-1129.
7. L. Bialy, J. J. Díaz-Mochón, E. Specker, L. Keinicke, M. Bradley, Tetrahedron 2005, 61, 8295-8305.
8. P.-Y. Kuo, D. -Y, Yang, J. Org. Chem. 2008, 73, 6455-6458.
9. I. A. Nash, B. W. Bycroft, W. C. Chan, Tetrahedron Lett. 1996, 37, 2625-2628.
10. B. Kellam, B. W. Bycroft, W. C. Chan, S. R. Chhabra, Tetrahedron 1998, 54, 6817-6832.
11. M. Alaiz, J. Giron, F. J. Hidalgo, M. P. Maza, F. Millan, R. Zamora, E. Vioque, Synthesis 1989, 544-547.
12. A. Gómez-Sánchez, P. B. Moya, J. Bellanato, Carbohydr. Res. 1984, 135, 101.
13. In a similar method 4 equiv of ethylenediamine was used to deprotect tetrachlorophthaloyl group, J. S. Debenham, B. Fraser-Reid, J. Org. Chem. 1996, 61, 432-433.
14. A. S. Noravyan, E. G. Paronikyan, S. A. Vartanyan, Farmaco Ed. Sci. 1980, 35, 1052-1058.
15. S. Lovro, S. Sonja, T. Renata, S. Branko, Heterocycles 1998, 47, 1017-1022.
16. E. Lager, P. Andersson, J. Nilsson, I. Pettersson, E. O. Nielsen, M. Nielsen, O. Sterner, T. Liljefors, J. Med. Chem. 2006, 49, 2526-2533.
17. B. A. Lucero, C. R. B. Gomes, I. C. P. P. Frugulhetti, L. V. Faro, L. Alvarenga, M. C. B. V. Souza, T. M. L. Souza, V. F. Ferreira, Bioorg. Med. Chem. Lett. 2006, 16, 1010-1013.
18. D. Edmont, R. Rocher, C. Plisson, J. Chenault, Bioorg. Med. Chem. Lett. 2000, 10, 1831-1834.
19. W. E. Parham, L. J. Reed, Org. Synth. 1955, 3, 395.
20. A. J. Boulton. A. McKillop, Comprehensive Heterocyclic Chemistry, Vol. 2, Pergamon Press, Oxford, 1984, pp. 404.
21. H. Hoga, A. Itoh, S. Murayama, S. Suzue, T. Irikura, J. Org. Chem. 1980, 45, 1358-1363.
22. H. R. Snyder, H. E. Frier, J. Am. Chem. Soc. 1946, 68, 1320-1322.
23. R. Ramesh, S. Chandrasekaran, Org. Lett. 2005, 7, 4947-4950.
24. A. Saha, B. Ranu, J. Org. Chem. 2008, 73, 6867-6870.
25. S. Amedov, A. S. Rzaev, Zh. Obshch. Khim. 1963, 33, 3842-3846.