New chiral Schiff base as a tridentate ligand for catalytic enantioselective addition of diethylzinc to aldehydes

Journal of Organic Chemistry

Volumn 71, Issue 18, 2006, Pages 7091-7093

  Tanaka, Takanori ^a   Yasuda, Yorinobu ^a   Hayashi, Masahiko ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; ALDEHYDES; CATALYSTS;

DIETHYLZINC; ENANTIOMERIC EXCESS (EE); ENANTIOSELECTIVE ADDITION; SCHIFF BASE;

MOLECULAR STRUCTURE;

1 PHENYL 1 PROPANOL; ALDEHYDE; DIETHYLZINC; LIGAND; PROPANOL; SCHIFF BASE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; LIGAND BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 33750463376     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060964u     Document Type: Article

References (20)

1. Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823-2824.
2. (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19-37.
3. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
4. (c) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
5. (d) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757-824.
6. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, Inc.: New York, 1994; Chapter 5.
7. (a) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5237-5240.
8. (b) Cherng, Y.-J.; Fang, J.-M.; Lu, T.-J. J. Org. Chem. 1999, 64, 3207-3212.
9. (c) Danilova, T. I.; Rozenberg, V. I.; Sergeeva, E. V.; Starikova, Z. A.; Bräse, S. Tetrahedron: Asymmetry 2003, 14, 2013-2019.
10. (a) Hayashi, M.; Tanaka, K.; Oguni, N. Tetrahedron: Asymmetry 1995, 6, 1833-1836.
11. (b) Hayashi, M.; Yoshimoto, K.; Hirata, N.; Tanaka, K.; Oguni, N.; Harada, K.; Matsushita, A.; Kawachi, Y.; Sasaki, H. Isr. J. Chem. 2001, 41, 241-246.
12. (a) Hayashi, M.; Yamada, K.; Nakayama, S. Synthesis 1999, 1869-1871.
13. (b) Hayashi, M.; Yamada, K.; Nakayama, S. J. Chem. Soc., Perkin Trans. 1 2000, 1501-1503.
14. (a) McKennon, M. J.; Meyers, A. I.; Drauz, K.; Schwarm, M. J. Org. Chem. 1993, 58, 3568-3571.
15. (b) Poindexter, G. S.; Meyers, A. I. Tetrahedron Lett. 1977, 18, 3527-3528.
16. Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 33, 5517-5518.
17. For determination of the absolute configuration of the products. See Supporting Information.
18. The reaction of dimethylzinc with benzaldehyde in the presence of 5 mol % of 5c in hexane afforded (R)-1-phenylethanol in 72% yield and in 64% ee (30 °C, 24 h).
19. Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
20. Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877-7878.