Synthesis of chiraphos via asymmetric hydrogenation of 2,3- bis(diphenylphosphinoyl)-buta-1,3-diene

Chemical Communications

Volumn , Issue 2, 2000, Pages 155-156

  Beghetto, Valentina ^a   Matteoli, Ugo ^a   Scrivanti, Alberto ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; HYDROGENATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034695594     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908447i     Document Type: Article

References (12)

1. U. Matteoli, V. Beghetto, C. Schiavon, A. Scrivanti and G. Menchi, Tetrahedron: Asymmetry, 1997, 8, 1403.
2. Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, New York, 1993.
3. H. Muramatstu, H. Kawano, Y. Ishii, M. Saburi and Y. Uchida, J. Chem. Soc., Chem. Commun., 1989, 769.
4. K. Mashima, K. Kusano, T. Ohta, R. Noyori and H. Takaya, J. Chem. Soc., Chem. Commun., 1989, 1208.
5. M. Kitamura, M. Tokunaga and R. Noyori, J. Org. Chem., 1992, 57, 4053.
6. Polarimetry measurements on different recrystallised samples of 2 have shown that there is no variation in the op due to recrystallisation from benzene - n-hexane.
7. 3) chemical shifts of the mixture containing the two diastereoisomers may be observed due to variations in sample concentration.
8. M. Kitamura, M. Tokunaga, T. Ohkuma and R. Noyori, Tetrahedron Lett., 1991, 32, 4163.
9. A. S. Chan, J. J. Pluth and J. Halpern, J. Am. Chem. Soc., 1980, 102, 5952; H. Kawano, T. Ikariya, Y. Ishii, S. Yoshikawa, Y. Uchida and H. Kumobayashi, J. Chem. Soc., Perkin Trans. 1, 1989, 1571.
10. A. S. Chan, J. J. Pluth and J. Halpern, J. Am. Chem. Soc., 1980, 102, 5952; H. Kawano, T. Ikariya, Y. Ishii, S. Yoshikawa, Y. Uchida and H. Kumobayashi, J. Chem. Soc., Perkin Trans. 1, 1989, 1571.
11. We are indebted to a referee for this suggestion.
12. 3, appt t, X part of an AA′X (A and A′ are the P atoms) spin system], 128.6 (C, arom, appt t), 131.4 (C, arom, appt t), 131.9 (C, s, arom.), 133.3 (C, s, arom.), 145.3 (C=, quin, AA′X spin system). Owing to the high symmetry of the molecule, the NMR data do not allow determination of the stereochemistry of the molecule.