A novel chiral pentamine ligand for enantioselective α-alkylation of acyclic lithium amide enolates. Optimization of chiral ligands for asymmetric reactions using solid-phase organic synthesis

Organic Letters

Volumn 1, Issue 2, 1999, Pages 345-347

  Matsuo, Jun Ichi ^a   Odashima, Kazunori ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000162732     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990624d     Document Type: Article

References (32)

1. For reviews see: (a) Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983-1984; Vol 3, pp 1-110.
2. (b) Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol 3, pp 1-63.
3. (c) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995.
4. (a) Evans, D. A.; Takacs, J. M. Tetrahedron Lett. 1980, 21, 4233-4236.
5. (b) Evans, D. A.; Takacs, J. M.; McGee, L. R.; Ennis, M. D.; Mathre, D. J.; Bartroli, J. Pure Appl. Chem. 1981, 53, 1109-1127.
6. (c) Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
7. (d) Evans, D. A. Aldrichim. Acta 1982, 15, 23-32.
8. (e) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603-5606.
9. Phase transfer catalyzed alkylation: Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001 and references therein.
10. Palladium-catalyzed reaction: (a) Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113-120.
11. (b) Genet, J. P.; Ferroud, D.; Juge, F. S.; Montes, J. R. Tetrahedron Lett. 1986, 27, 4573-4576.
12. (c) Sawamura, M.; Nagata, H.; Sakamoto, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 2586-2592.
13. (d) Trost, B. M.; Radinov, R.; Grenzer, E. M. J. Am. Chem. Soc. 1997, 119, 7879-7880.
14. (e) Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918-1919.
15. (a) Review: Koga, K.; Shindo, M. J. Synth. Org. Chem. Jpn. 1995, 53, 1021-1032.
16. (b) Murakata, M.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1990, 1657-1658.
17. (c) Hasegawa, Y.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1993, 34, 1963-1966.
18. (d) Yasukata, T.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 35-38.
19. (e) Imai, M.; Hagihara, A.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829-8830.
20. (f) Yasuda, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1996, 37, 6343-6346.
21. (g) Yasuda, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1997, 38, 3531-3534.
22. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7579-7592.
23. (i) Murakata, M.; Yasukata, T.; Aoki, T.; Nakajima, M.; Koga, K. Tetrahedron 1998, 54, 2449-2458.
24. (j) Matsuo, J.; Kobayashi, S.; Koga, K. Tetrahedron Lett. 1998, 39, 9723-9726.
25. (k) Yamashita, Y.; Odashima, K.; Koga, K. Tetrahedron Lett. 1999, 40, 2803-2806.
26. (a) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712-7713.
27. (b) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901-4902.
28. (c) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704-1707 and references therein.
29. (a) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290.
30. (b) Matsuo, J.; Koga, K. Chem. Pharm. Bull. 1997, 45, 2122-2124.
31. 3)) was determined by acidic hydrolysis to (S)-α-benzylpropionic acid (Helmchen, G.; Nill, G.; Flockerzi, D.; Youssef, M. S. K. Angew. Chem., Int. Ed. Engl. 1979, 18, 63-65).
32. 21NO: 231.1623. Found: 231.1605.