New chiral ligands derived from (S)-leucine for the enantioselective addition of diethylzinc to aldehydes

Tetrahedron

Volumn 56, Issue 2, 2000, Pages 175-178

  Kawanami, Yasuhiro ^a   Mitsuie, Tomoko ^a   Miki, Misuzu ^a   Sakamoto, Takanobu ^a   Nishitani, Kazumi ^a  

^a KAGAWA UNIVERSITY   (Japan)

Author keywords

(S) leucine; Chiral ligands; Enantioselective addition

Indexed keywords

ALDEHYDE; AMINOALCOHOL; DIETHYLZINC; LEUCINE; LIGAND; METHANOL; PIPERIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034614560     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00971-0     Document Type: Article

References (22)

1. (a) Gwley, R. E.; Aube, J. Principles of Asymmetric Synthesis; Pergamon: London, 1996.
2. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
3. (c) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995.
4. Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823.
5. For review, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
6. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
7. Kitamura M., Suga S., Kawai K., Noyori R. J. Am. Chem. Soc. 108:1986;6071.
8. Soai K., Ookawa A., Kaba T., Ogawa K. J. Am. Chem. Soc. 109:1987;7111.
9. Soai K., Yokoyama S., Hayasaka T. J. Org. Chem. 56:1991;4264.
10. Delair P., Einhorn C., Einhorn J., Luche J.L. Tetrahedron. 51:1995;165.
11. Beliczey J., Giffels G., Kragl U., Wandrey C. Tetrahedron: Asymmetry. 8:1997;1529.
12. Partly presented at the 74th Meeting of Japan Chemical Society, Kyoto, March 1998, Abstr. No. 2, 1D6 02 (p 982) and the 76th Meeting, Kanagawa, March 1999, Abstr. No. 2, 4C1 18 (p 976). During the preparation of this manuscript, a study of an excellent ligand for aliphatic aldehydes has been reported; Sola, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J. J. Org. Chem. 1998, 63, 7078.
13. Partly presented at the 74th Meeting of Japan Chemical Society, Kyoto, March 1998, Abstr. No. 2, 1D6 02 (p 982) and the 76th Meeting, Kanagawa, March 1999, Abstr. No. 2, 4C1 18 (p 976). During the preparation of this manuscript, a study of an excellent ligand for aliphatic aldehydes has been reported; Sola, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J. J. Org. Chem. 1998, 63, 7078.
14. Partly presented at the 74th Meeting of Japan Chemical Society, Kyoto, March 1998, Abstr. No. 2, 1D6 02 (p 982) and the 76th Meeting, Kanagawa, March 1999, Abstr. No. 2, 4C1 18 (p 976). During the preparation of this manuscript, a study of an excellent ligand for aliphatic aldehydes has been reported; Sola, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J. J. Org. Chem. 1998, 63, 7078.
15. The norephedrine bearing a 2-phenylethyl substituent on the amino moiety provided no asymmetric induction for the addition of diethylzinc to nonanal (Ref. 5), although the amino alcohol with a 4-phenylethyl substituent was reported to be an effective catalyst for the addition of difurylzinc; Soai, K.; Kawase, Y. J. Chem. Soc., Perkin Trans. 1 1990, 3214.
16. Zhang H., Xue F., Mak T.C.W., Chan K.S. J. Org. Chem. 61:1996;8002.
17. (a) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
18. (b) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6237.
19. (c) Kitamura, M.; Yamakawa, M.; Oka, H.; Suga, S.; Noyori, R. Chem. Eur. J. 1996, 2, 1173.
20. (d) Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800.
21. (e) Kitamura, M.; Oka, H.; Noyori, R. Tetrahedron 1999, 55, 3605.
22. Bull S.D., Davies S.G., Fox D.J., Garner C., Sellers T.G.R. Pure & Appl. Chem. 70:1998;1501.