Complete reversal of enantioselection using oxazoline-containing Schiff base ligands derived from l-serine in enantioselective addition of diketene to aldehydes

Tetrahedron Asymmetry

Volumn 17, Issue 18, 2006, Pages 2672-2677

  Chu, Changhu ^a   Morishita, Koji ^a   Tanaka, Takanori ^a   Hayashi, Masahiko ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; FURFURAL; KETENE DERIVATIVE; OXAZOLINE DERIVATIVE; SCHIFF BASE; SERINE;

ADDITION REACTION; ARTICLE; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 33750521340     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.09.026     Document Type: Article

References (23)

1. Hayashi M., Miyamoto Y., Inoue T., and Oguni N. J. Chem. Soc., Chem. Commun. (1991) 1752-1753
2. Hayashi M., Miyamoto Y., Inoue T., and Oguni N. J. Org. Chem. 58 (1993) 1515-1522
3. Hayashi M., Inoue T., and Oguni N. J. Chem. Soc., Chem. Commun. (1994) 341-342
4. Hayashi M., Inoue T., Miyamoto Y., and Oguni N. Tetrahedron 50 (1994) 4385-4398
5. Hayashi M., Tanaka K., and Oguni N. Tetrahedron: Asymmetry 6 (1995) 1833-1836
6. Hayashi M., Yoshimoto K., Hirata N., Tanaka K., Oguni N., Harada K., Matsushita A., Kawachi Y., and Sasaki H. Isr. J. Chem. 41 (2001) 241-246
7. After our first report on the reaction of aldehyde with diketene, see:. Yanagisawa A., Matsumoto Y., Asakawa K., and Yamamoto H. J. Am. Chem. Soc. 121 (1999) 892-893
8. Yanagisawa A., Matsumoto Y., Asakawa K., and Yamamoto H. Tetrahedron 58 (2002) 8331-8339
9. Kawase T., Takizawa S., Jayaprakash D., and Sasai H. Synth. Commun. 34 (2004) 4487-4492
10. Mareno R.M., and Moyano A. Tetrahedron: Asymmetry 17 (2006) 1104-1110
11. For the synthesis of salicyloxazoline ligand, see:. Brunner H., and Berghofer J. J. Organomet. Chem. 501 (1995) 161-166
12. Xu C., and Yuan C. Tetrahedron 61 (2005) 2169-2186
13. Gd versus Ti:. Yabu K., Matsumoto S., Yamasaki S., Hamashima Y., Kanai M., Du W., Curran D.P., and Shibasaki M. J. Am. Chem. Soc. 123 (2001) 9908-9909
14. Yb versus Zr:. Hamashima Y., Kanai M., Du W., Curran D.P., and Shibasaki M. J. Am. Chem. Soc. 123 (2001) 9908-9909
15. Cu versus Ni:. Shibata N., Ishimaru T., Nagai T., Kohno J., and Toru T. Synlett (2004) 1703-1706
16. Cu versus Zn:. Du D.-M., Lu S.-F., Fang T., and Xu J. J. Org. Chem. 70 (2005) 3712-3715
17. Kanai M., Nakagawa Y., and Tomioka K. Tetrahedron 55 (1999) 3831-3842
18. Fernandez A.I., Fraile J.M., Garcia J.I., Herrerias C.I., Mayoral J.A., and Salvatella L. Catal. Commun. 2 (2001) 165-170
19. Casey C.P., Martins S.C., and Fagan M.A. J. Am. Chem. Soc. 126 (2004) 5585-5592
20. Altava B., Burguete M.I., Fraile J.M., Garcia J.I., Luis S.V., Mayoral J.A., Royo A.J., and Vicent M.J. Tetrahedron: Asymmetry 8 (1997) 2561-2570
21. Li X.-G., Chen X., Ma J.-A., and Zhou Q.-L. J. Organomet. Chem. 640 (2001) 65-71
22. The notations of R and S are different in entries 5 and 7, because of the priority of substituents. The same enantiomeric face of aldehyde was selected by the use of 1a or 2b.
23. Hayashi M., Nakamura N., and Yamashita K. Tetrahedron 60 (2004) 6777-6783