An efficient diastereoselective synthesis of chiral ferrocenyl aldehydes

Tetrahedron

Volumn 54, Issue 41, 1998, Pages 12539-12546

  Lu, Xiyan ^a   Chen, Guoying ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 [1' N,N DIMETHYLAMINOETHYL] 2 FORMYLFERROCENE; ALDEHYDE DERIVATIVE; FERROCENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CONFORMATIONAL TRANSITION; ENANTIOMER; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032497678     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00733-9     Document Type: Article

References (25)

1. 1. a) Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395.
2. b) Hayashi, T.; Isaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153.
3. c) Hayashi, T.; Karehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113.
4. d) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649.
5. e) Hayashi, T.; Sawamura, M.; Ito, Y. Tetrahedron 1992, 48, 1999.
6. f) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 593.
7. g) Sawamura, M.; Yamauchi, A.; Takegawa, T.; Ito, Y. J. Chem. Soc. Chem. Commun. 1991, 874.
8. 2. a) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. J. Org. Chem. 1991, 56, 2218.
9. b) Sawamura, M.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295.
10. 3. Lio, H.; Fujii, A.; Ishii, M.; Tokoroyama, T. J. Chem. Soc. Chem. Commun. 1991, 1390.
11. 4. Schlogl, K. J. Organomet. Chem. 1986, 300, 219 and references cited therein.
12. 5. Marquarding, D.; Klusacek, H.; Gokel, G. W.; Hoffmann, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389.
13. 6. Gokel, G. W.; Ugi, I. K. J. Chem. Educ. 1972, 49, 294.
14. 7. Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835.
15. 8. Togni, A.; Rihs, G. Organometallics, 1993, 12, 3368.
16. 9. a) Wakefield, B. J. Organolithium Methods, Academic Press: New York, 1988.
17. b) Wakefield, B. J. The Chemistry of Organolithium Compounds, Pergamon: Oxford, 1974.
18. c) Houben-Weyl. Methoden der Organischen Chemie, 4th ed., Vol. XIII/1; Thieme: Stuggart, 1974.
19. d) Schlosser, M. Polare Organometalle; Springer: Berlin, 1973.
20. 10. Ahn, K. H.; Cho, C-W.; Baek, H-H.; Park, J.; Lee. S. J. Org. Chem. 1996, 61, 4937.
21. 11. During the preparation of the manuscript, a paper of synthesis of racemic 1-dimethylaminoethyl-2-fomylferrocene using DMF as the electrophile was published. See Malfait, S.; Pélinski, L.; Maciejewski, L.; Brocard, J. Synlett 1997, 830.
22. 12. a) Drew, J.; Letellier, M.; Morand, P.; Szabo, A. G. J. Org. Chem. 1987, 52, 4047.
23. b) Huang, Y.; Shen, Y.; Zheng, J.; Zhang, S. Synthesis 1985, 57-58.
24. 13. a) Gokel, G. W.; Marquarding, D; Ugi, I. K. J. Org. Chem. 1972, 37, 3052.
25. b) Togni, A.; Breutel, C.; Schingder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062.