Asymmetric Michael Reaction of α-Cyano Esters Catalyzed by Chiral Rh(I) Complexes with a New Optically Active Bisphosphine Ligand

Synlett

Volumn 1997, Issue 1, 1997, Pages 119-120

  Inagaki, Kohji ^a   Nozaki, Kyoko ^a   Takaya, Hidemasa ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041350014     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-712     Document Type: Article

References (17)

1. (a) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S. -I. J. Am. Chem. Soc. 1989, 111, 5954.
2. (b) Murahashi, S. -I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436.
3. (c) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807.
4. (a) Sawamura, M.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295.
5. (b) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron 1994, 50, 4439.
6. (c) Sawamura, M.; Hamashima, H.; Shinoto, H.; Ito, Y. Tetrahedron Lett. 1995, 36, 6479.
7. 2: C, 81.11; H, 5.67. Found: C, 81.23; H, 5.83.
8. (a) Horiuchi, T.; Ohta, T.; Stephane, M.; Takaya, H. Tetrahedron: Asymmetry 1994, 5, 325.
9. (b) Reeder, J.; Castro, P. P.; Knobler, C. B.; Martinborough, E.; Owens, L.; Diederich, F. J. Org. Chem. 1994, 59, 3151.
10. (c) Hester, M. R.; Uyeki, M. A.; Diederich, F. Isr. J. Chem. 1989, 29, 201.
11. Rh-P = 142.7 Hz).
12. For a large P-P coupling constant of 354.8 Hz in a Rh(I) complex containing trans-chelating bisphosphine ligand, see: Sawamura, M.; Hamashima, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549.
13. For P-P coupling constants of 113-116 Hz in a Rh(I) complex with chelating bisphosphine ligand having the bite angle of 124.8 °, see: Casey, C. P.; Whiteker, G. T.; Melville, M. G.; Petrovich, L. M.; Gavney, Jr., J. A.; Powell, D. R. J. Am. Chem. Soc. 1992, 114, 5535.
14. Rh-P = 126.7 Hz). Free acetylacetone was observed in the reaction of 6 with 3a.
15. Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309.
16. 11 None of the bond length was fixed from the beginning.
17. Casey, C. P.; Whiteker, G. T. Isr. J. Chem. 1990, 30, 299.