Ligand effects on the diastereoselectivities of samarium diiodide promoted pinacol coupling

European Journal of Organic Chemistry

Volumn , Issue 3, 1999, Pages 565-572

  Pedersen, Henriette Lodberg ^a   Christensen, Torben Birk ^a   Enemærke, Rasmus Juel ^a   Daasbjerg, Kim ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

1,2 Diols; Aldehydes; Diastereoselectivity; Pinacol coupling; Samarium diiodide

Indexed keywords

BENZALDEHYDE DERIVATIVE; CYCLOHEXANECARBALDEHYDE DERIVATIVE; SAMARIUM; SAMARIUM DIIODIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; DIASTEREOISOMER; DIMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032792039     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (45)

1. For several reviews on the pinacol coupling: [1a] T. Wirth, Angew. Chem. 1996, 108, 65; Angew. Chem., Int. Ed. Engl. 1996, 35, 61
2. For several reviews on the pinacol coupling: [1a] T. Wirth, Angew. Chem. 1996, 108, 65; Angew. Chem., Int. Ed. Engl. 1996, 35, 61
3. [1b] R. G. Dushin, in Comprehensive Organometallic Chemistry II (Ed.: L. S. Hegedus), Pergamon, Oxford, 1995, vol. 12, p. 1071.
4. [1c] A. Fürstner, Angew. Chem. 1993, 105, 171; Angew. Chem., Int. Ed. Engl. 1993, 32, 164.
5. [1c] A. Fürstner, Angew. Chem. 1993, 105, 171; Angew. Chem., Int. Ed. Engl. 1993, 32, 164.
6. [1d] G. M. Robertson, in Comprehensive Organic Synthesis (Ed.: B. M. Trost), Pergamon, New York, 1991, vol. 3, p. 563.
7. [1e] J. E. McMurray, Chem. Rev. 1989, 89, 1513.
8. [1f] B. E. Kahn, R. D. Rieke, Chem. Rev. 1988, 88, 733.
9. [2a] J. L. Namy, J. Souppe, H. B. Kagan, Tetrahedron Lett. 1983, 24, 765.
10. [2b] J. Souppe, L. Danon, J. L. Namy, H. B. Kagan, J. Organomet. Chem. 1983, 250, 227.
11. [2c] T. Honda, M. Katoh, Chem. Commun. 1997, 369.
12. [2d] R. Nomura, T. Matsuno, T. Endo, J. Am. Chem. Soc. 1996, 118, 11666.
13. [2e] N. Miyoshi, S. Takeuchi, Y. Ohgo, Chem. Lett. 1993, 2129.
14. N. Taniguchi, N. Kaneta, M. Uemura, J. Org. Chem. 1996, 61, 6088.
15. N. Taniguchi, M. Uemura, Tetrahedron Lett. 1998, 39, 5385.
16. [5a] T. Imamoto, T. Takeyama, M. Yokoyama, Tetrahedron Lett. 1984, 25, 3225.
17. [5b] T. Imamoto, T. Hatajima, N. Takiyama, T. Takeyama, Y. Kamiya, T. Yoshizawa, J. Chem. Soc., Perkin Trans. 1 1991, 3127.
18. [6a] R. D. Rogers, R. D. Etzenhouser, J. S. Murdoch, Inorganica Chimica Acta 1992, 196, 73.
19. [6b] R. D. Rogers, R. D. Etzenhouser, J. S. Murdoch, E. Reyes, Inorg. Chem. 1991, 30, 1445.
20. [6c] R. D. Rogers, A. N. Rollins, M. M. Benning, Inorg. Chem. 1988, 27, 3826.
21. [6d] R. D. Rogers, L. K. Kurihara, Inorg. Chem. 1987, 26, 1498.
22. [6e] A. Sen, V. Chebolu, A. L. Rheingold, Inorg. Chem. 1987, 26, 1821.
23. J.-S. Shiue, C.-C. Lin, J.-M. Fang, Tetrahedron Lett. 1993, 34, 335.
24. [8a] D. F. Evans, G. V. Fazakerley, R. F. Phillips, J. Chem. Soc. A 1971, 1931.
25. [8b] J. L. Namy, P. Girard, H. B. Kagan, P. Caro, Nouv. J. Chim. 1981, 5, 479.
26. [8c] Y. Okaue, T. Isobe, Inorg. Chem. Acta 1988, 144, 143.
27. [6b]). In this structure, the oxygen atoms of tetraglyme are all nearly coplanar and lie in the equatorial plane of the complex.
28. W. J. Evans, T. S. Gummersheimer, J. W. Ziller, J. Am. Chem. Soc. 1995, 119, 8999.
29. [12]) The sterically hindered aryloxide groups only allow the coordination of two THF molecules, hence making it difficult to make a comparison of our results with those of Hou et al.
30. Z. Hou, T. Miyano, H. Yamazaki, Y. Wakatsuki, J. Am. Chem. Soc. 1995, 117, 4421.
31. J. R. Fuchs, M. L. Mitchell, M. Shabangi, R. A. Flowers II, Tetrahedron Lett. 1997, 38, 8175.
32. [15]).
33. A. Lebrun, J. L. Namy, H. B. Kagan, Tetrahedron Lett. 1993, 34, 2311.
34. [16a] O. Jarreton, T. Skrydstrup, J.-M. Beau, Chem. Commun. 1996, 1661.
35. [16b] T. Skrydstrup, O. Jarreton, D. Mazéas, D. Urban, J.-M. Beau, Chem. Eur. J. 1998, 4, 655.
36. [16c] D. Urban, T. Skrydstrup, J.-M. Beau, J. Org. Chem. 1998, 63, 2507.
37. [16d] T. Skrydstrup, D. Mazéas, M. Elmouchir, G. Doisneau, C. Riche, A. Chiaroni, J.-M. Beau, Chem. Eur. J. 1997, 8, 1342.
38. [16e] D. Urban, T. Skrydstrup, J.-M. Beau, Chem. Commun. 1998, 955.
39. [1] and the following references: [17a] M. C. Barden, J. Schwartz, J. Am. Chem. Soc. 1996, 118, 5484.
40. [17b] A. Gansäuer, Chem. Commun. 1997, 457.
41. [17c] T. A. Lipski, M. A. Hilfiker, S. G. Nelson, J. Org. Chem. 1997, 62, 4566.
42. [17d] T. Harao, B. Hatano, M. Asahara, Y. Muguruma, A. Ogawa, Tetrahedron Lett. 1998, 39, 5247.
43. [17e] M. C. Barden, J. Schwartz, J. Org. Chem. 1997, 62, 7520.
44. [17f] A. Gansäuer, M. Moschioni, D. Bauer, Eur. J. Org. Chem. 1998, 1923.
45. J. L. Namy, P. Girard, H. B. Kagan, J. Am. Chem. Soc. 1980, 102, 2693.