An L-proline-based β-amino tertiary thiol: Synthesis and use as a catalyst in the enantioselective addition of diethylzinc to aldehydes

Tetrahedron Asymmetry

Volumn 10, Issue 8, 1999, Pages 1551-1561

  Gibson, Colin L ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINOALCOHOL; PROLINE; THIOL DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYST; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0033597421     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00151-2     Document Type: Article

References (43)

1. 1. (a) Hof, R. P; Poelert, M. A.; Peper, N. C. M. W.; Kellogg, R. M. Tetrahedron: Asymmetry 1994, 5, 31-34;
2. (b) Fitzpatrick, K.; Hulst, R.; Kellogg, R. M. Tetrahedron: Asymmetry 1995, 6, 1861-1864.
3. 2. (a) Kang, J.; Lee, D. J. W.; Kim, J. I. Chem. Commun. 1994, 2009-2010;
4. (b) Kang, J.; Kim, D. S.; Kim, J. I. Synlett. 1994, 842-844;
5. (c) Kang, J.; Kim, J. B.; Kim, J. W.; Lee, D. J. Chem Soc., Perkin Trans. 2 1997, 189-194.
6. 3. (a) Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391-1401;
7. (b) Iwasa, K.; Hongo, H, Heterocycles 1997, 46, 267-274.
8. 4. Chelucci, G.; Berta, D.; Fabbri, D.; Pinna, G. A.; Saba, A.; Ulgheri, F. Tetrahedron: Asymmetry 1998, 9, 1933-1940.
9. 5. Gibson, C. L. Chem. Commun. 1996, 645-646.
10. 6. Gibson, C. L. Tetrahedron: Asymmetry 1996, 7, 3357-3358.
11. 7. Cran, G. A.; Gibson, C. L.; Handa, S.; Kennedy, A. R. Tetrahedron: Asymmetry 1996, 7, 2511-2514.
12. 8. Fulton, D. A.; Gibson, C. L. Tetrahedron Lett. 1997, 38, 2019-2022.
13. 9. (a) Rijnberg, E.; Jastrzebski, J. T. B. H.; Janssen, M. D.; Boersma, J.; van Koten, G. Tetrahedron Lett. 1994, 35, 6521-6524;
14. (b) Satoh, Y; Makihara, T.; Shi, M. Chem Pharm Bull. 1996, 44, 454-456;
15. (c) Hulst, R.; Heres, H.; Fitzpatrick, K.; Peper, N. C. M. W.; Kellogg, R. M. Tetrahedron: Asymmetry 1996, 7, 2755-2760;
16. (d) Jin, M.-J.; Ahn, S.-J.; Lee, K.-S. Tetrahedron Lett. 1996, 37, 8767-8770;
17. (e) Rijnberg, E.; Hovestad, N. J.; Kleij, A. W.; Jastrzebski, J. T. B. H.; Boersma, J.; Janssen, M. D.; Spek, A. L.; van Koten, G. Organomet. 1997, 16, 2847-2857;
18. (f) Anderson, J. C.; Cubbon, R.; Harding, M.; James, D. S. Tetrahedron: Asymmetry 1998, 9, 3461-3490.
19. 10. Cran, G. A.; Gibson, C. L.; Handa, S. Tetrahedron: Asymmetry 1995, 6, 1553-1556.
20. 11. In related amino aryl diselenides, Wirth et al. have unequivocally established, by isolation, that an ethyl selenide (45% yield) is obtained upon treatment with diethylzinc. This ethyl selenide was proven not to be the dominant catalytically active species in the addition of diethylzinc to benzaldehycle (17% yield). Furthermore, these workers also provided NMR evidence for zinc sclenolate dimers: Wirth, T.; Kulicke, K. J.; Fragale, G. Helv. Chim. Acta 1996, 79, 1957-1966.
21. 12. Improvements in enantioselectivities in numerous diarylhydroxymethyl containing catalysts over their hydroxymethanol counterparts have been recorded but tor a recent review sec: Braun, M. An gew. Chem., Int. Ed. Engl. 1996, 35, 519-522.
22. 13. Soai, K.; Ookawa, H.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 709, 7111-7115.
23. 14. (a) Kellogg, R. M.; Hof, R. P. J. Chem. Soc. Perkm Trans. 1 1996, 1651-1657;
24. (b) Koning, B.; Hulst, R.; Bouter, A., Butcr, J.; Meetsma, A.; Kellogg, R. M. Chem. Commun. 1997, 1065-1066;
25. (c) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540.
26. 15. Seebach, D.; Beck, A. K.; Hayakawa, M.; Jaescke, G.; Kühne, F. N. M.; Nägeli, I.; Pinkerton, A. B., Rheiner, P. B.; Duthaler, R. O.; Rothe, P. M.; Weigand, W.; Wünsch, R.; Dick, S.; Nespar, R.; Wörle, M.; Gramlich, V. Bull. Soc. Chim Fr. 1997, 134, 315-331.
27. 16. Seebach, D.; Jaescke, G.; Pichota, A.; Audergon, L. Helv. Chim. Acta 1997, 80, 2515-2519.
28. 17. (a) Kanth, J. V. B.; Periasamy, M. Tetrahedron 1993, 49, 5127-5132,
29. (b) Bailey, D. J.; O'Hagan, D.; Tavasli, M. Tetrahedron: Asymmetry 1997, 8, 149-153;
30. (c) Delaunay, D.; Le Corre, M. J. Chem. Soc., Perkin Trans, 1 1994, 3041-3042.
31. 18. Deyrup, J. A.; Moyer, C. L.; Dreifus, P. S. J. Org. Chem. 1970, 35, 3428-3432.
32. 19. Nishio, T. J. Chem. Soc.. Perkin Trans, 1 1993, 1113-1117.
33. 20. Gauthier, J. Y; Bourdon, F.; Young, R. L. N. Tetrahedron Lett. 1986, 27, 15-18.
34. 21. Baudouin, C. M. Phil. Thesis; University of Strathclyde, September, 1998.
35. 22. (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856;
36. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 46-69.
37. 23. Yamakawa, M.; Noyori, R. J. Am Chem. Soc. 1995, 117, 6327-6335.
38. 24. Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1997, 50, 8773-8776.
39. 25. Goldfuss, B.; Houk, K. N. J. Org. Chem. 1998, 63, 8998-9006.
40. 26. Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530-2435.
41. 27. The term ami ami Re refers to the fact that in transition states 11a.b the bicyclo[2,2,0] core is anti to both the pyrrolidine ring and thiazazincolidine ring and that alkyl delivery is to the Re face of the aldehyde. In the case of the transition states 12a,b the description syn anti Si refers to the fact that the bicyclo[2,2,0] core is syn to the pyrrolidine ring and anti to the thiazazincolidine ring, alkyl delivery is to the Si face of the aldehyde.
42. 28. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
43. 29. Fletcher, D. A.; McMeeking, R. F.; Parkin, D. Chem. Inf. Comput. Sci. 1996, 36, 746-749.