Enantioselective hydrophosphonylation of aldehydes using an aluminum binaphthyl Schiff base complex as a catalyst

Synlett

Volumn , Issue 12, 2007, Pages 1960-1962

  Ito, Katsuji ^a   Tsutsumi, Hironori ^a   Setoyama, Masayuki ^a   Saito, Bunnai ^b   Katsuki, Tsutomu ^b  

^a FUKUOKA UNIVERSITY OF EDUCATION   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

hydroxy phosphonate; Aluminum; Asymmetric catalysis; Binaphthyl Schiff bases; Hydrophosphonylation

Indexed keywords

4 CHLOROBENZALDEHYDE; ALDEHYDE DERIVATIVE; ALUMINUM BINAPHTHYL; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY;

EID: 34547641254     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984528     Document Type: Article

References (25)

1. Reviews: (a) Wiemer, D. F. Tetrahedron 1997, 53, 16609.
2. (b) Groger, H.; Hammer, B. Chem. Eur. J. 2000, 6, 943; and references cited therein.
3. (a) Yokomatsu, T.; Yamagichi, T.; Shibuya, S. Tetrahedron: Asymmetry 1993, 4, 1779.
4. (b) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1993, 4, 1783.
5. (c) Rath, N. P.; Spilling, C. D. Tetrahedron Lett. 1994, 35, 227.
6. (d) Arai, T.; Bougauchi, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926.
7. (e) Yokomatsu, T.; Yamagichi, T.; Matsumoto, K.; Shibuya, S. Tetrahedron 1996, 52, 11725.
8. (f) Sasai, H.; Bougauchi, M.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 2717.
9. (g) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1997, 1527.
10. (h) Groaning, M. D.; Rowe, B. J.; Spilling, C. D. Tetrahedron Lett. 1998, 39, 5485.
11. (i) Cermak, D. M.; Du, Y.; Wiemer, D. F. J. Org. Chem. 1999, 64, 388.
12. (j) Yamagishi, T.; Yokomatsu, T.; Suemune, K.; Shibuya, S. Tetrahedron 1999, 52, 12125.
13. (k) Skropeta, D.; Schmidt, R. R. Tetrahedron: Asymmetry 2003, 14, 265.
14. (a) Duxbury, J. P.; Cawley, A.; Thornton-Pett, M.; Wantz, L.; Warne, J. N. D.; Greatrex, R.; Brown, D.; Kee, T. P. Tetrahedron Lett. 1999, 40, 4403.
15. (b) Ward, C. V.; Jiang, M.; Kee, T. P. Tetrahedron Lett. 2000, 41, 6181.
16. (c) Duxbury, J. P.; Warne, J. N. D.; Mushtaq, R.; Ward, C.; Thornton-Pett, M.; Jiang, M.; Greatrex, R.; Kee, T. P. Organometallics 2000, 19, 4445.
17. (d) Nixon, T. D.; Dalgarno, S.; Ward, C. V.; Jiang, M.; Halcrow, M. A.; Kilner, C.; Thornton-Pett, M.; Kee, T. P. C. R. Chim. 2004, 7, 809.
18. (a) Saito, B.; Katsuki, T. Angew. Chem. Int. Ed. 2005, 44, 4600.
19. (b) Saito, B.; Egami, H.; Katsuki, T. J. Am. Chem. Soc. 2007, 129, 1978.
20. Fe and Mn binaphthyl-Schiff base complexes have been reported to possess cis-β configuration: Cheng, M.-C.; Chang, M. C.-W.; Peng, S.-M.; Cheung, K.-K.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1997, 3479.
21. (a) Uchida, T.; Katsuki, T. Tetrahedron Lett. 2001, 42, 6911.
22. (b) Uchida, T.; Katsuki, T.; Ito, K.; Akashi, S.; Ishii, A.; Kuroda, T. Helv. Chim. Acta 2002, 85, 3078.
23. Complexes 2 were prepared according to the reported procedure (ref. 4).
24. The cationic complex of 2c has been reported to be an efficient catalyst for enantioselective aldol reactions of aldehydes and 5-alkoxyoxazoles. See: Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem. Int. Ed. 2001, 40, 1884.
25. 4 and concentrated. Silica gel chromatography of the residue (hexane-EtOAc, 7:3 to 1:1) gave the desired product (19.5 mg, 78%) as an oil. The ee of the product was determined to be 84% by HPLC using chiral stationary phase column as described in the footnote to Table 1.