An approach to the synthesis of platinum complexes containing chiral monodentate phosphines with simultaneous regeneration of the resolving agent

Organometallics

Volumn 16, Issue 15, 1997, Pages 3561-3564

  Albert, Joan ^a   Granell, Jaume ^a   Mínguez, Jorge ^a   Muller, Guillermo ^a   Sainz, Daniel ^a   Valerga, Pedro ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF CÁDIZ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000834182     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970176i     Document Type: Article

References (39)

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2. For recent references on chiral phosphines, see: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375. (b) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow R. L. J. Am. Chem. Soc. 1993, 175, 10125. (c) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. J. Am. Chem. Soc. 1992, 114, 9327.
3. For recent references on chiral phosphines, see: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375. (b) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow R. L. J. Am. Chem. Soc. 1993, 175, 10125. (c) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. J. Am. Chem. Soc. 1992, 114, 9327.
4. For recent reviews on asymmetric catalysis, see: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: Weinheim, 1993. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994.
5. For recent reviews on asymmetric catalysis, see: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: Weinheim, 1993. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994.
6. For recent references in this subject see: (a) Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. (b) Choi, S. Y. M.; Siah, S.; Leung, P; Mok, K. F. Inorg. Chem. 1993, 32, 4812. (c) Gabbitas, N.; Salem, G.; Sterns, M.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1993, 3271. (d) Aw, B.; Leung, P. Tetrahedron: Asymmetry 1994, 5, 1167. (e) Ramsden, J. A.; Brown, J. M.; Hursthouse, M. B.; Karaulov, A. I. Tetrahedron: Asymmetry 1994, 5, 2033. (f) Doyle, R. J.; Salem, G.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1995, 1867. (g) Leiten, J.; Salem, G.; Hockless, D. C. R. J. Chem. Soc., Dalton Trans. 1995, 649.
7. For recent references in this subject see: (a) Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. (b) Choi, S. Y. M.; Siah, S.; Leung, P; Mok, K. F. Inorg. Chem. 1993, 32, 4812. (c) Gabbitas, N.; Salem, G.; Sterns, M.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1993, 3271. (d) Aw, B.; Leung, P. Tetrahedron: Asymmetry 1994, 5, 1167. (e) Ramsden, J. A.; Brown, J. M.; Hursthouse, M. B.; Karaulov, A. I. Tetrahedron: Asymmetry 1994, 5, 2033. (f) Doyle, R. J.; Salem, G.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1995, 1867. (g) Leiten, J.; Salem, G.; Hockless, D. C. R. J. Chem. Soc., Dalton Trans. 1995, 649.
8. For recent references in this subject see: (a) Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. (b) Choi, S. Y. M.; Siah, S.; Leung, P; Mok, K. F. Inorg. Chem. 1993, 32, 4812. (c) Gabbitas, N.; Salem, G.; Sterns, M.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1993, 3271. (d) Aw, B.; Leung, P. Tetrahedron: Asymmetry 1994, 5, 1167. (e) Ramsden, J. A.; Brown, J. M.; Hursthouse, M. B.; Karaulov, A. I. Tetrahedron: Asymmetry 1994, 5, 2033. (f) Doyle, R. J.; Salem, G.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1995, 1867. (g) Leiten, J.; Salem, G.; Hockless, D. C. R. J. Chem. Soc., Dalton Trans. 1995, 649.
9. For recent references in this subject see: (a) Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. (b) Choi, S. Y. M.; Siah, S.; Leung, P; Mok, K. F. Inorg. Chem. 1993, 32, 4812. (c) Gabbitas, N.; Salem, G.; Sterns, M.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1993, 3271. (d) Aw, B.; Leung, P. Tetrahedron: Asymmetry 1994, 5, 1167. (e) Ramsden, J. A.; Brown, J. M.; Hursthouse, M. B.; Karaulov, A. I. Tetrahedron: Asymmetry 1994, 5, 2033. (f) Doyle, R. J.; Salem, G.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1995, 1867. (g) Leiten, J.; Salem, G.; Hockless, D. C. R. J. Chem. Soc., Dalton Trans. 1995, 649.
10. For recent references in this subject see: (a) Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. (b) Choi, S. Y. M.; Siah, S.; Leung, P; Mok, K. F. Inorg. Chem. 1993, 32, 4812. (c) Gabbitas, N.; Salem, G.; Sterns, M.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1993, 3271. (d) Aw, B.; Leung, P. Tetrahedron: Asymmetry 1994, 5, 1167. (e) Ramsden, J. A.; Brown, J. M.; Hursthouse, M. B.; Karaulov, A. I. Tetrahedron: Asymmetry 1994, 5, 2033. (f) Doyle, R. J.; Salem, G.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1995, 1867. (g) Leiten, J.; Salem, G.; Hockless, D. C. R. J. Chem. Soc., Dalton Trans. 1995, 649.
11. For recent references in this subject see: (a) Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. (b) Choi, S. Y. M.; Siah, S.; Leung, P; Mok, K. F. Inorg. Chem. 1993, 32, 4812. (c) Gabbitas, N.; Salem, G.; Sterns, M.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1993, 3271. (d) Aw, B.; Leung, P. Tetrahedron: Asymmetry 1994, 5, 1167. (e) Ramsden, J. A.; Brown, J. M.; Hursthouse, M. B.; Karaulov, A. I. Tetrahedron: Asymmetry 1994, 5, 2033. (f) Doyle, R. J.; Salem, G.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1995, 1867. (g) Leiten, J.; Salem, G.; Hockless, D. C. R. J. Chem. Soc., Dalton Trans. 1995, 649.
12. For recent references in this subject see: (a) Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743. (b) Choi, S. Y. M.; Siah, S.; Leung, P; Mok, K. F. Inorg. Chem. 1993, 32, 4812. (c) Gabbitas, N.; Salem, G.; Sterns, M.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1993, 3271. (d) Aw, B.; Leung, P. Tetrahedron: Asymmetry 1994, 5, 1167. (e) Ramsden, J. A.; Brown, J. M.; Hursthouse, M. B.; Karaulov, A. I. Tetrahedron: Asymmetry 1994, 5, 2033. (f) Doyle, R. J.; Salem, G.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1995, 1867. (g) Leiten, J.; Salem, G.; Hockless, D. C. R. J. Chem. Soc., Dalton Trans. 1995, 649.
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23. 2-PCH(OMe)Ph, see Muller, G.; Sainz, D. J. Organomet. Chem. 1995, 495, 103 and Oehme, H.; Leissring, E. Tetrahedron 1981, 37, 753, respectively.
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27. A signal at δ = 25.5, corresponding to the phosphine oxide, is also observed when the reaction is carried on 6b.
28. Albert, J.; Granell, J.; Muller, G.; Sainz, D.; Font-Bardia, M.; Solans, X. Tetrahedron: Asymmetry 1995, 6, 325.
29. 3)] was obtained. Probably the use of the palladium complex 6b, as a phosphine source, assures a low concentration of this ligand in solution, that prevents the formation of the mixtures of coordination complexes.
30. The intensity of the signals in the NMR spectrum of 7 shows that this reaction does not change the optical enrichment of the phosphine.
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37. 2PCH(OMe)Ph is readily oxidizable and should be stored under nitrogen but, when coordinated to palladium, this ligand becomes very stable and can be stored several months in air.
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