An efficient diastereoselective synthesis of chiral oxazolinylferrocene compounds

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 4937-4943

  Ahn, Kyo Han ^a   Cho, Chang Woo ^a   Baek, Hyon Ho ^a   Park, Jaiwook ^a   Lee, Sunwoo ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000065342     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960198z     Document Type: Article

References (36)

1. (a) Hayashi, T.; Tajika, M.; Tamao, K.; Kumada, M. J. Am. Chem. Soc. 1976, 98, 3718.
2. (b) Hayashi, T.; Konishi, M.; Fukushima, M.; Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180.
3. (c) Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395.
4. (d) Hayashi, T.; Konishi, M.; Okamoto, Y.; Kabeta, K.; Kumada, M. J. Org. Chem. 1986, 51, 3772.
5. (a) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405.
6. (b) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1986, 28, 6215.
7. (c) Pastor, S. D.; Togni, A. J. Am. Chem. Soc. 1989, 111, 2333.
8. (d) Hayashi, T. Pure & Appl. Chem. 1988, 60, 7 and references therein.
9. (e) Sawamura, M.; Ito, Y.; Hayashi, T. Tetrahedron Lett. 1989, 30, 2247.
10. Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389.
11. (a) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835.
12. (b) Using a chiral sulfoxide as the directing group, see: Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568.
13. For recent reviews: (a) Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356.
14. (b) Snieckus, V. Chem. Rev. 1990, 90, 879.
15. These results were presented at the 74th Annual Meeting of the Korean Chemical Society, Chungju, Chungbuk, Korea, October 1994; paper ORGN C17.
16. (a) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10.
17. (b) Richards, C.; Damalidis, T.; Hibbs, D. E.; Hursthose, M. B. Synlett 1995, 74.
18. (c) Nishibashi, Y.; Uemura, S. Synlett 1995, 79.
19. (d) Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-W. Tetrahedron Lett. 1995, 36, 7263.
20. Rebiere, F.; Samuel, O.; Kagan, H. B. Tetrahedron Lett. 1990, 31, 3121.
21. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 4171.
22. This mild protocol has been used by Meyers (Meyers, A. I.; Robichaud, A. J.; McKennon, M. J. Tetrahedron Lett. 1992, 33, 1181: see the footnote 10). Recently Sammakia has also used this method (see the supporting information of ref 7a).
23. The described synthesis of oxazoline compounds from carboxylic acid esters is applicable to the synthesis of other oxazoline compounds such as (S)-(-)-2,2′-isopropylidenebis(4-isopropyl-2-oxazoline) (Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726) and 2-(2-bromophenyl)-4-isopropyl-2-oxazoline (Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769) in greater than 90% yield. For an enolizable ester such as malonic acid dimethyl ester, the transamidation did not occur.
24. The described synthesis of oxazoline compounds from carboxylic acid esters is applicable to the synthesis of other oxazoline compounds such as (S)-(-)-2,2′-isopropylidenebis(4-isopropyl-2-oxazoline) (Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726) and 2-(2-bromophenyl)-4-isopropyl-2-oxazoline (Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769) in greater than 90% yield. For an enolizable ester such as malonic acid dimethyl ester, the transamidation did not occur.
25. Richards and Uemura synthesized these compounds, independently, but with a quite different selectivity (see references 7b and 7c). The selectivity obtained by us is similar to that obtained by Richards (2.5:1).
26. 2 complex has been reported recently: Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745. (b) The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
27. 2 complex has been reported recently: Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745. (b) The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
28. 1H NMR analysis for the crude products.
29. A full manuscript is in preparation.
30. Meyers, A. I.; Shimano, M. Tetrahedron Lett. 1993, 34, 4893.
31. For a recent study on the stability of t-BuLi in THF and related references, see: Stanetty, P.; Koller, H.; Mihovilovic, M. J. Org. Chem. 1992, 57, 6833.
32. The instability of lithiated ferrocene itself in THF is reported during our study: Guillaneux, D.; Kagan, H. B. J. Org. Chem. 1995, 60, 2502.
33. 2 chromatography is delayed for overnight at 5°C, a lower yield is obtained, possibly owing to the oxidation of the phosphine compound.
34. Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002: Discussion about the directed lithiation mechanism with related references and an excellent demonstration for the N-directed lithiation are included in this paper.
35. Kofron, W. G.; Baclawski, L. M.; Ronald, R. C. J. Org. Chem. 1976, 41, 1879.
36. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.