Diastereoselective synthesis of diphosphines, effect of their configuration in asymmetric catalysis

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4713-4716

  Pellon, Pascal ^a   Le Goaster, Celine ^a   Toupet, Loic ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030199694     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00948-3     Document Type: Article

References (16)

1. 1. Noyori R., Asymmetric Catalysis in Organic Synthesis ; John Wiley and Sons ; New-York, 1994. Kagan H.B., C. R. Acad. Sci., 1996, 322, serie IIb, 131. Imamoto T., Tsuruta H., Wada Y., Masuda H., Yamaguchi K., Tetrahedron Lett., 1995, 36, 8271. Kless A., Kadyrov R., Börner A., Holz J., Kagan H.B., Tetrahedron Lett., 1995, 36, 4601.
2. 1. Noyori R., Asymmetric Catalysis in Organic Synthesis ; John Wiley and Sons ; New-York, 1994. Kagan H.B., C. R. Acad. Sci., 1996, 322, serie IIb, 131. Imamoto T., Tsuruta H., Wada Y., Masuda H., Yamaguchi K., Tetrahedron Lett., 1995, 36, 8271. Kless A., Kadyrov R., Börner A., Holz J., Kagan H.B., Tetrahedron Lett., 1995, 36, 4601.
3. 1. Noyori R., Asymmetric Catalysis in Organic Synthesis ; John Wiley and Sons ; New-York, 1994. Kagan H.B., C. R. Acad. Sci., 1996, 322, serie IIb, 131. Imamoto T., Tsuruta H., Wada Y., Masuda H., Yamaguchi K., Tetrahedron Lett., 1995, 36, 8271. Kless A., Kadyrov R., Börner A., Holz J., Kagan H.B., Tetrahedron Lett., 1995, 36, 4601.
4. 1. Noyori R., Asymmetric Catalysis in Organic Synthesis ; John Wiley and Sons ; New-York, 1994. Kagan H.B., C. R. Acad. Sci., 1996, 322, serie IIb, 131. Imamoto T., Tsuruta H., Wada Y., Masuda H., Yamaguchi K., Tetrahedron Lett., 1995, 36, 8271. Kless A., Kadyrov R., Börner A., Holz J., Kagan H.B., Tetrahedron Lett., 1995, 36, 4601.
5. 2. Gourdel Y., Pellon P., Toupet L., Le Corre M., Tetrahedron Lett., 1994, 35, 1197.
6. 3. Takamo S., Kurotaki A., Ogasawara T., Synthesis , 1987, 1075. Takamo S., Kurotaki A., Ogasawara T., Takahashi M., Synthesis, 1986, 403.
7. 3. Takamo S., Kurotaki A., Ogasawara T., Synthesis , 1987, 1075. Takamo S., Kurotaki A., Ogasawara T., Takahashi M., Synthesis, 1986, 403.
8. 4. Kagan H.B. and al., Bull. Soc. Chim. Belg., 1979, 11, 923.
9. 2 : C, 66.14; H, 6.91; P, 8.94. Found : C, 66.31; H, 6.74; P, 8.91.
10. 2 : C, 66.14; H, 6.91; P, 8.94. Found : C, 66.24; H, 6.86; P, 9.24.
11. -1, F(000) = 414, T = 293 K, final R = 0.055 for 2583 observations.
12. 8. Brisset H., Gourdel Y., Pellon P., Le Corre M., Tetrahedron lett., 1994, 34, 4523.
13. aromatics); 173.0 (CO).
14. 10. Birbaum S.M., Levintov L., Kingsley R.B, Greenstein J.P., J. Biol. Chem., 1952, 194, 455.
15. 2 (0.0014 mmol), of ligand (0.030 mmol), and of α-acetamidoacrylic acid (1.120 mmol) in 2.6 mL of MeOH in the hydrogenation flask, was stirred under hydrogen atmospher during the appropriate time. The solution was evaporated to dryness. The residue was dissolved in water and separated from the insoluble catalyst by filtration. Evaporation to dryness afforded the N-acetyl alanine.
16. 31P NMR were performed on a Brucker AC 300 spectrometer, in deuteriochloroform, using the solvent as internal reference. Optical rotations were recorded on Perkin Elmer 241 MC polarimeter. Melting points were determined on a Kofler hot stage apparatus. Silica gel (70-230 mesh) for column chromatography was purchased from Merck.