Chiral 2-(1-dimethylaminoethyl)ferrocenecarbaldehyde as an effective catalyst for asymmetric alkylation of aldehydes with dialkylzinc

Synlett

Volumn , Issue 7, 1998, Pages 727-728

  Fukuzawa, Shin Ichi ^a   Kato, Hirohisa ^a  

^a CHUO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002370084     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1776     Document Type: Article

References (18)

1. For reviews, a) Ferrocenes; Togni, A.; Hayashi, T., Eds.; VCH: Weinheim, 1995.
2. b) Kagan, H. B.; Riant, O. In Advances in Asymmetric Synthesis Vol 2; Hassner, A., Ed.; JAI: London, 1997; pp189-235.
3. c) Togni, A. Angew. Chem. Int. Ed. Engl. 1996, 35, 1475.
4. d) Kagan, H. B.; Diter, P.; Gref. A.; Guillaneux, D.; Masson-Szymczak, A.; Rebiere, F.; Riant, O.; Samuel, O.; Tauden, S. Pure&Appl. Chem. 1996, 68, 29.
5. Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733.
6. 19FeNO: C, 63.17; H, 6.72; N, 4.91. Found: C, 63.15; H, 6.74; N, 6.69.
7. For reviews, a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
8. b) Butsugan, Y.; Araki, S.; Watanabe, M. In Ferrocenes; Hayashi, T.; Togni, A. Eds.; VCH: Weinheim, 1995; pp143-168.
9. c) Erdik, E. Organozinc Reagents in Organic Synthesis; CRC: Boca Raton, 1996.
10. d) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley; New York, 1994; Chap 5.
11. 25FeNO: C, 64.77; H, 7.99; N, 4.44. Found: C, 64.81; H, 7.96; N, 4.41.
12. Taudien, S.; Riant, O.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 3513. Highly diastereoselective addition of organometallic reagents to chiral ferrocenecarbaldehydes will be reported in due course.
13. Trapping of α-lithio ferrocene of 1 with an aldehyde gives a diastereomeric mixture of a ferrocenyl amino alcohol with a low diastereoraeric excess. Bauelle, L. F.; Bau, R.; Oyakawa, R. T.; Ugi, I. K. J. Am. Chem. Soc. 1973, 95, 482;
14. Watanabe, M.; Araki, S.; Butugan, Y.; Uemura, J. Org. Chem. 1991, 56, 2218.
15. Samakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10;
16. Richard, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74;
17. 2: C, 62.79; H, 5.89; N, 4.31. Found: C, 62.75; H, 5.94; N, 4.35.
18. Kitajima, H.; Ito, K.; Aoki, Y. and Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207.