Indium mediated allylation of glyoxylate oxime ethers, esters and cyanoformates

Organic and Biomolecular Chemistry

Volumn 2, Issue 13, 2004, Pages 1921-1933

  Ritson, Dougal J ^a   Cox, Russell J ^a   Berge, John ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; DERIVATIVES; HIGH TEMPERATURE EFFECTS; INDIUM; ISOMERS; MIXTURES; ORGANIC ACIDS;

LEWIS ACIDS; REAGENTS; SPECIES;

AROMATIC COMPOUNDS;

EID: 3142714522     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b402764g     Document Type: Article

References (40)

1. For reviews see: R. Bloch, Chem. Rev., 1998, 98, 1407; D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 1997, 8, 1895.
2. For reviews see: R. Bloch, Chem. Rev., 1998, 98, 1407; D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 1997, 8, 1895.
3. K. C. Nicolaou, H. J. Mitchell, F. L. van Delft, F. Rubsam and R. M. Rodriguez, Angew. Chem., Int. Ed., 1998, 37, 1871 ; D. Wang, L. Dai, X. Hou and Y. Zhang, Tetrahedron Lett., 1996, 37, 4187; E. Ciganek, J. Org. Chem., 1992, 57, 4521; A. Hirao, I. Hattori, K. Yamaguchi and S. Nakahama, Synthesis, 1982, 461.
4. K. C. Nicolaou, H. J. Mitchell, F. L. van Delft, F. Rubsam and R. M. Rodriguez, Angew. Chem., Int. Ed., 1998, 37, 1871 ; D. Wang, L. Dai, X. Hou and Y. Zhang, Tetrahedron Lett., 1996, 37, 4187; E. Ciganek, J. Org. Chem., 1992, 57, 4521; A. Hirao, I. Hattori, K. Yamaguchi and S. Nakahama, Synthesis, 1982, 461.
5. K. C. Nicolaou, H. J. Mitchell, F. L. van Delft, F. Rubsam and R. M. Rodriguez, Angew. Chem., Int. Ed., 1998, 37, 1871 ; D. Wang, L. Dai, X. Hou and Y. Zhang, Tetrahedron Lett., 1996, 37, 4187; E. Ciganek, J. Org. Chem., 1992, 57, 4521; A. Hirao, I. Hattori, K. Yamaguchi and S. Nakahama, Synthesis, 1982, 461.
6. K. C. Nicolaou, H. J. Mitchell, F. L. van Delft, F. Rubsam and R. M. Rodriguez, Angew. Chem., Int. Ed., 1998, 37, 1871 ; D. Wang, L. Dai, X. Hou and Y. Zhang, Tetrahedron Lett., 1996, 37, 4187; E. Ciganek, J. Org. Chem., 1992, 57, 4521; A. Hirao, I. Hattori, K. Yamaguchi and S. Nakahama, Synthesis, 1982, 461.
7. G. Stork and S. R. Dowd, J. Am. Chem. Soc., 1963, 85, 2178.
8. H. M. Kissman, D. S. Tarbell and J. Williams, J. Am. Chem. Soc., 1953, 75, 2959.
9. Y. Yamaoto, T. Komatsu and K. Maruyama, J. Org. Chem., 1985, 50, 3115.
10. R. W. Hoffman and A. Endesfelder, Liebigs Ann. Chem., 1987, 215.
11. D. S. Brown, P. T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin and E. Swann, Tetrahedron, 1995, 51, 11473.
12. Y. Yamamoto and W. Ito, Tetrahedron, 1988, 44, 5415.
13. S. Hanessian and R. Y. Yang, Tetrahedron Lett., 1996, 37(30), 5273.
14. D. J. Ritson, Synthetic Pages, 2002, http://www.syntheticpages.org/pages/ 203
15. S. Araki, H. Ito and Y. Butsugan, J. Org. Chem., 1988, 53, 1831.
16. For examples of In allylations see: L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc., 1996, 118, 1917; S. Araki, T. Shimizu, P. S. Johar, S. Jin and Y. Butsugan, J. Org. Chem., 1991, 56, 2538. For aqueous reactions and the utilisation of indium in more complex synthesis see: T. Loh, G. Cao and J. Pei, Tetrahedron Lett., 1998, 39, 1453; M. B. Isaac and L. A. Paquette, J. Org. Chem., 1997, 62, 5333; D. M. Gordon and G. M. Whitesides, J. Org. Chem., 1993, 53, 7937; T. Chan and C. Li, J. Chem. Soc., Chem. Commun., 1992, 747.
17. For examples of In allylations see: L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc., 1996, 118, 1917; S. Araki, T. Shimizu, P. S. Johar, S. Jin and Y. Butsugan, J. Org. Chem., 1991, 56, 2538. For aqueous reactions and the utilisation of indium in more complex synthesis see: T. Loh, G. Cao and J. Pei, Tetrahedron Lett., 1998, 39, 1453; M. B. Isaac and L. A. Paquette, J. Org. Chem., 1997, 62, 5333; D. M. Gordon and G. M. Whitesides, J. Org. Chem., 1993, 53, 7937; T. Chan and C. Li, J. Chem. Soc., Chem. Commun., 1992, 747.
18. For examples of In allylations see: L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc., 1996, 118, 1917; S. Araki, T. Shimizu, P. S. Johar, S. Jin and Y. Butsugan, J. Org. Chem., 1991, 56, 2538. For aqueous reactions and the utilisation of indium in more complex synthesis see: T. Loh, G. Cao and J. Pei, Tetrahedron Lett., 1998, 39, 1453; M. B. Isaac and L. A. Paquette, J. Org. Chem., 1997, 62, 5333; D. M. Gordon and G. M. Whitesides, J. Org. Chem., 1993, 53, 7937; T. Chan and C. Li, J. Chem. Soc., Chem. Commun., 1992, 747.
19. For examples of In allylations see: L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc., 1996, 118, 1917; S. Araki, T. Shimizu, P. S. Johar, S. Jin and Y. Butsugan, J. Org. Chem., 1991, 56, 2538. For aqueous reactions and the utilisation of indium in more complex synthesis see: T. Loh, G. Cao and J. Pei, Tetrahedron Lett., 1998, 39, 1453; M. B. Isaac and L. A. Paquette, J. Org. Chem., 1997, 62, 5333; D. M. Gordon and G. M. Whitesides, J. Org. Chem., 1993, 53, 7937; T. Chan and C. Li, J. Chem. Soc., Chem. Commun., 1992, 747.
20. For examples of In allylations see: L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc., 1996, 118, 1917; S. Araki, T. Shimizu, P. S. Johar, S. Jin and Y. Butsugan, J. Org. Chem., 1991, 56, 2538. For aqueous reactions and the utilisation of indium in more complex synthesis see: T. Loh, G. Cao and J. Pei, Tetrahedron Lett., 1998, 39, 1453; M. B. Isaac and L. A. Paquette, J. Org. Chem., 1997, 62, 5333; D. M. Gordon and G. M. Whitesides, J. Org. Chem., 1993, 53, 7937; T. Chan and C. Li, J. Chem. Soc., Chem. Commun., 1992, 747.
21. For examples of In allylations see: L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc., 1996, 118, 1917; S. Araki, T. Shimizu, P. S. Johar, S. Jin and Y. Butsugan, J. Org. Chem., 1991, 56, 2538. For aqueous reactions and the utilisation of indium in more complex synthesis see: T. Loh, G. Cao and J. Pei, Tetrahedron Lett., 1998, 39, 1453; M. B. Isaac and L. A. Paquette, J. Org. Chem., 1997, 62, 5333; D. M. Gordon and G. M. Whitesides, J. Org. Chem., 1993, 53, 7937; T. Chan and C. Li, J. Chem. Soc., Chem. Commun., 1992, 747.
22. S. Jin, S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1993, 66, 1528.
23. H. M. S. Kumar, S. Anjaneyulu, E. J. Reddy and J. S. Yadav, Tetrahedron Lett., 2000, 41, 9311.
24. K. Hammer and K. Undheim, Tetrahedron, 1997, 53, 2309.
25. T. S. Cooper, P. Laurent, C. J. Moody and A. K. Takle, Org. Biomol. Chem., 2004, 265-276.
26. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.
27. K. Katagiri, H. Nochi, A. Kurimoto, H. Sato and C. Kaneko, Chem. Pharm. Bull., 1994, 42(6), 1251.
28. D. Home, J. Gaudino and W. J. Thompson, Tetrahedron Lett., 1984, 33, 3529.
29. S. Yamago, M. Nakamura, X. Q. Wang, M. Yanagawa, S. Tokumitsu and E. Nakamur, J. Org. Chem., 1998, 63, 1694.
30. N. Subasinghe, M. Schulte, M. Y. M. Chan, R. J. Roon, J. F. Koerner and R. L. Johnson, J. Med. Chem., 1990, 33, 2734.
31. A. R. Jurgens, K. Green, E. R. Ruso, M. N. Jennings, D. M. Blum and G. B. Feigelson, Synth. Commun., 1994, 24, 1171.
32. L. A. Carpino, J. Org. Chem., 1964, 29, 2820.
33. S. Torrente and R. Alonso, Org. Lett., 2001, 3, 1985.
34. M. Moreno-Manas, M. Perez and R. Pleixats, Tetrahedron, 1994, 50(2), 515.
35. N. Jacobsen, H. Kolind-Andersen and J. Christensen, Can. J. Chem., 1984, 62, 1940.
36. R. H. Prager, J. A. Smith, B. Weber and C. M. Williams, J. Chem. Soc., Perkin Trans. 1, 1997, 2659.
37. R. E. Gawley and T. Nagg, Tetrahedron Lett., 1984, 25(3), 263.
38. J. I. Bhat, W. Clegg, H. Maskill, M. R. J. Elsegood, I. D. Menneer and P. C. Miatt, J. Chem. Soc., Perkin Trans. 2, 2000, 1435.
39. B. R. Cho, H. S. Chung and N. S. Cho, J. Org. Chem., 1998, 63, 4685.
40. D. R. Boyd, J. F. Malone and M. R. McGuckin, J. Chem. Soc., Perkin Trans. 2, 1988, 1145.