Detritylation Procedure under Non-Acidic Conditions: Naphthalene Catalysed Reductive Cleavage of Trityl Ethers

Synthesis

Volumn , Issue 14, 2003, Pages 2179-2184

  Yus, Miguel ^a   Behloul, Cherif ^a   Guijarro, David ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Detritylation; Lithiation; Lithium; Reductive cleavage; Trityl ether

Indexed keywords

ALCOHOLS; CATALYSIS; ETHERS; LITHIUM; NAPHTHALENE; REDUCTION;

DETRITYLATION;

SYNTHESIS (CHEMICAL);

ETHER DERIVATIVE; LITHIUM DERIVATIVE; NAPHTHALENE; OXYGEN; TRITYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; DETRITYLATION; LITHIATION; METHODOLOGY;

EID: 0142025314     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41057     Document Type: Article

References (48)

1. (a) Helferich, B. Adv. Carbohydr. Chem. 1948, 3, 79.
2. (b) Dekker, C. A.; Goodman, L. In Chemistry and Biochemistry, Vol. IIA: Pigman, W.; Horton, D., Eds.; Academic Press: New York, 1970, 22.
3. (a) Bodanszky, M.; Onetti, O. A. Peptide Synthesis; Interscience: New York, 1966, 36.
4. (b) Bodanszky, M. Principles in Peptide Synthesis; Springer-Verlag: New York, 1993, 2nd ed., 88.
5. Köster, H.; Hoppe, N.; Kohli, V.; Kröpelin, M.; Kaut, H.; Kulikowski, K. Nucleic Acids Symp. Ser. 1980, 7, 39.
6. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1999, 103.
7. Kunz, H.; Waldmann, H. In Comprehensive Organic Synthesis, Vol. 6; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991, 650.
8. Imagawa, H.; Tsuchihashi, T.; Singh, R. K.; Yamamoto, H.; Sugihara, T.; Nishizawa, M. Org. Lett. 2003, 5, 153.
9. Rele, S.; Nayak, S. K. Synth. Commun. 2002, 32, 3533.
10. Hwu, J. R.; Jain, M. L.; Tsai, F.-Y.; Tsay, S.-C.; Balakumar, A.; Hakimelahi, G. H. J. Org. Chem. 2000, 65, 5077.
11. For reviews see: (a) Yus, M. Chem. Soc. Rev. 1996, 25, 155. (b) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225. (c) Yus, M. Synlett 2001, 1197. (d) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79. (e) Ramón, D. J.; Yus, M. Rev. Cubana Quim. 2002, 14, 76. (f) Yus, M. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Mareck, I., Eds.; J. Wiley & Sons: Chichester, 2003. (g) For a mechanistic study see: Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455. (h) See also: Yus, M.; Herrera, R. P.; Guijarro, A. Chem.-Eur. J. 2002, 8, 2574. (i) See also:Herrera, R. P.; Guijarro, A.; Yus, M. Tetrahedron Lett. 2003, 44, 1309.
12. For reviews see: (a) Yus, M. Chem. Soc. Rev. 1996, 25, 155. (b) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225. (c) Yus, M. Synlett 2001, 1197. (d) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79. (e) Ramón, D. J.; Yus, M. Rev. Cubana Quim. 2002, 14, 76. (f) Yus, M. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Mareck, I., Eds.; J. Wiley & Sons: Chichester, 2003. (g) For a mechanistic study see: Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455. (h) See also: Yus, M.; Herrera, R. P.; Guijarro, A. Chem.-Eur. J. 2002, 8, 2574. (i) See also:Herrera, R. P.; Guijarro, A.; Yus, M. Tetrahedron Lett. 2003, 44, 1309.
13. For reviews see: (a) Yus, M. Chem. Soc. Rev. 1996, 25, 155. (b) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225. (c) Yus, M. Synlett 2001, 1197. (d) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79. (e) Ramón, D. J.; Yus, M. Rev. Cubana Quim. 2002, 14, 76. (f) Yus, M. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Mareck, I., Eds.; J. Wiley & Sons: Chichester, 2003. (g) For a mechanistic study see: Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455. (h) See also: Yus, M.; Herrera, R. P.; Guijarro, A. Chem.-Eur. J. 2002, 8, 2574. (i) See also:Herrera, R. P.; Guijarro, A.; Yus, M. Tetrahedron Lett. 2003, 44, 1309.
14. For reviews see: (a) Yus, M. Chem. Soc. Rev. 1996, 25, 155. (b) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225. (c) Yus, M. Synlett 2001, 1197. (d) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79. (e) Ramón, D. J.; Yus, M. Rev. Cubana Quim. 2002, 14, 76. (f) Yus, M. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Mareck, I., Eds.; J. Wiley & Sons: Chichester, 2003. (g) For a mechanistic study see: Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455. (h) See also: Yus, M.; Herrera, R. P.; Guijarro, A. Chem.-Eur. J. 2002, 8, 2574. (i) See also:Herrera, R. P.; Guijarro, A.; Yus, M. Tetrahedron Lett. 2003, 44, 1309.
15. For reviews see: (a) Yus, M. Chem. Soc. Rev. 1996, 25, 155. (b) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225. (c) Yus, M. Synlett 2001, 1197. (d) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79. (e) Ramón, D. J.; Yus, M. Rev. Cubana Quim. 2002, 14, 76. (f) Yus, M. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Mareck, I., Eds.; J. Wiley & Sons: Chichester, 2003. (g) For a mechanistic study see: Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455. (h) See also: Yus, M.; Herrera, R. P.; Guijarro, A. Chem.-Eur. J. 2002, 8, 2574. (i) See also:Herrera, R. P.; Guijarro, A.; Yus, M. Tetrahedron Lett. 2003, 44, 1309.
16. For reviews see: (a) Yus, M. Chem. Soc. Rev. 1996, 25, 155. (b) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225. (c) Yus, M. Synlett 2001, 1197. (d) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79. (e) Ramón, D. J.; Yus, M. Rev. Cubana Quim. 2002, 14, 76. (f) Yus, M. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Mareck, I., Eds.; J. Wiley & Sons: Chichester, 2003. (g) For a mechanistic study see: Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455. (h) See also: Yus, M.; Herrera, R. P.; Guijarro, A. Chem.-Eur. J. 2002, 8, 2574. (i) See also:Herrera, R. P.; Guijarro, A.; Yus, M. Tetrahedron Lett. 2003, 44, 1309.
17. For reviews see: (a) Yus, M. Chem. Soc. Rev. 1996, 25, 155. (b) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225. (c) Yus, M. Synlett 2001, 1197. (d) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79. (e) Ramón, D. J.; Yus, M. Rev. Cubana Quim. 2002, 14, 76. (f) Yus, M. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Mareck, I., Eds.; J. Wiley & Sons: Chichester, 2003. (g) For a mechanistic study see: Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455. (h) See also: Yus, M.; Herrera, R. P.; Guijarro, A. Chem.-Eur. J. 2002, 8, 2574. (i) See also:Herrera, R. P.; Guijarro, A.; Yus, M. Tetrahedron Lett. 2003, 44, 1309.
18. For reviews see: (a) Yus, M. Chem. Soc. Rev. 1996, 25, 155. (b) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225. (c) Yus, M. Synlett 2001, 1197. (d) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79. (e) Ramón, D. J.; Yus, M. Rev. Cubana Quim. 2002, 14, 76. (f) Yus, M. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Mareck, I., Eds.; J. Wiley & Sons: Chichester, 2003. (g) For a mechanistic study see: Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455. (h) See also: Yus, M.; Herrera, R. P.; Guijarro, A. Chem.-Eur. J. 2002, 8, 2574. (i) See also:Herrera, R. P.; Guijarro, A.; Yus, M. Tetrahedron Lett. 2003, 44, 1309.
19. For reviews see: (a) Yus, M. Chem. Soc. Rev. 1996, 25, 155. (b) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225. (c) Yus, M. Synlett 2001, 1197. (d) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79. (e) Ramón, D. J.; Yus, M. Rev. Cubana Quim. 2002, 14, 76. (f) Yus, M. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Mareck, I., Eds.; J. Wiley & Sons: Chichester, 2003. (g) For a mechanistic study see: Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455. (h) See also: Yus, M.; Herrera, R. P.; Guijarro, A. Chem.-Eur. J. 2002, 8, 2574. (i) See also:Herrera, R. P.; Guijarro, A.; Yus, M. Tetrahedron Lett. 2003, 44, 1309.
20. For a polymer-supported version of this reaction see: (a) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397. (b) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017. (c) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207.
21. For a polymer-supported version of this reaction see: (a) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397. (b) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017. (c) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207.
22. For a polymer-supported version of this reaction see: (a) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397. (b) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017. (c) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207.
23. For a review see: Guijarro, D.; Yus, M. Recent Res. Dev. Org. Chem. 1998, 2, 713.
24. For reviews see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155. (b) Nájera, C.; Yus, M. Recent Res. Dev. Org. Chem. 1997, 1, 67. (c) Nájera, C.; Yus, M. Curr. Org. Chem. 2003, 7, 867.
25. For reviews see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155. (b) Nájera, C.; Yus, M. Recent Res. Dev. Org. Chem. 1997, 1, 67. (c) Nájera, C.; Yus, M. Curr. Org. Chem. 2003, 7, 867.
26. For reviews see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155. (b) Nájera, C.; Yus, M. Recent Res. Dev. Org. Chem. 1997, 1, 67. (c) Nájera, C.; Yus, M. Curr. Org. Chem. 2003, 7, 867.
27. For a review see: Yus, M.; Foubelo, F. Rev. Heteroatom Chem. 1997, 17, 73.
28. (a) Guijarro, D.; Mancheño, B.; Yus, M. Tetrahedron 1992, 48, 4593.
29. (b) Guijarro, D.; Mancheño, B.; Yus, M. Tetrahedron Lett. 1992, 33, 5597.
30. (c) Guijarro, D.; Guillena, G.; Mancheño, B.; Yus, M. Tetrahedron 1994, 50, 3427.
31. (d) Guijarro, D.; Mancheño, B.; Yus, M. Tetrahedron 1994, 50, 8551.
32. (e) Guijarro, D.; Yus, M. Tetrahedron 1995, 51, 11445.
33. (f) Alonso, E.; Guijarro, D.; Yus, M. Tetrahedron 1995, 57, 11457.
34. (g) Alonso, E.; Ramón, D. J.; Yus, M. J. Org. Chem. 1997, 62, 417.
35. (h) Alonso, E.; Ramón, D. J.; Yus, M. Tetrahedron 1997, 53, 14355.
36. (i) Alonso, E.; Guijarro, D.; Martínez, P.; Ramón, D. J.; Yus, M. Tetrahedron 1999, 55, 11027.
37. For a review on the cleavage of ethers with organoalkali metal compounds and alkali metals see: Maercker, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 972.
38. The formation of orange-red solutions of the trityl radical in THF has been described in the literature. See for instance: Ashby, E. C.; Goel, A. B.; DePriest, R. N. J. Org. Chem. 1981, 46, 2429.
39. For reviews on CIPE see: (a) Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356. (b) Snieckus, V. Chem. Rev. 1990, 90, 879. (c) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.
40. For reviews on CIPE see: (a) Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356. (b) Snieckus, V. Chem. Rev. 1990, 90, 879. (c) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.
41. For reviews on CIPE see: (a) Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356. (b) Snieckus, V. Chem. Rev. 1990, 90, 879. (c) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.
42. Yus, M.; Martinez, P.; Guijarro, D. Tetrahedron 2001, 57, 10119.
43. Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165.
44. Colin-Messager, S.; Girard, J.-P.; Rossi, J.-C. Tetrahedron Lett. 1992, 33, 2689.
45. Chaudhary, S. K.; Hernández, O. Tetrahedron Lett. 1979, 95.
46. Freeman, P. K.; Siggel, L.; Chamberlain, P. H.; Clapp, G. E. Tetrahedron 1988, 44, 5051.
47. Jones, G. B.; Huber, R. S.; Chapman, B. J. Tetrahedron: Asymmetry 1997, 8, 1797.
48. Carganico, G.; Mauleón Casellas, D.; García Pérez, M. L. PCT Int. Appl. WO 9428004, 1994; Chem. Abstr. 1994, 123: 170071.