Synthesis of P,S,O-ligands incorporating a planar chiral ferrocenyl motif

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 41-44

  Spencer, John ^a   Gramlich, Volker ^a   Häusel, Robert ^b   Togni, Antonio ^a  

^a ETH ZURICH   (Switzerland)

^b CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030043225     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00416-5     Document Type: Article

References (22)

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3. (a) H.C.L. Abbenhuis, U. Burckhardt, V. Gramlich, A. Martelletti, J. Spencer, I. Steiner, A. Togni, to be submitted for publication.
4. See also; (b) T. Hayashi, A. Ohno, S. Lu, Y. Matsumoto, E. Fukuyo, K. Yanagi, J. Am. Chem. Soc. 1994, 116, 4221.
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8. (d) U. Burckhardt, L. Hintermann, A. Schnyder, A. Togni, Organometallics, in press.
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14. 1H NMR spectra are complex and under current investigation by 2D NMR methods. Satisfactory microanalyses for all compounds reported have been obtained.
15. For a review, see: (a) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089. For leading references see (b) P. von Matt, G. C. Lloyd-Jones, A.B.E. Mindis, A. Pfaltz, L. Macko, M. Neuberger, M. Zehnder, H. Rüegger and P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265 and refs. cited therein. For the use of chiral, sulphur-containing chelating ligands in Pd-allyl chemistry, see; (c) J. V. Allen, J. F. Bower, J. M. J. Williams, Tetrahedron: Asymmetry 1994, 5, 1895. (d) J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin, J. M. J. Williams, J. Chem. Soc. Perkin Trans. I 1994, 2065. (e) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 55, 1523.
16. For a review, see: (a) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089. For leading references see (b) P. von Matt, G. C. Lloyd-Jones, A.B.E. Mindis, A. Pfaltz, L. Macko, M. Neuberger, M. Zehnder, H. Rüegger and P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265 and refs. cited therein. For the use of chiral, sulphur-containing chelating ligands in Pd-allyl chemistry, see; (c) J. V. Allen, J. F. Bower, J. M. J. Williams, Tetrahedron: Asymmetry 1994, 5, 1895. (d) J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin, J. M. J. Williams, J. Chem. Soc. Perkin Trans. I 1994, 2065. (e) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 55, 1523.
17. For a review, see: (a) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089. For leading references see (b) P. von Matt, G. C. Lloyd-Jones, A.B.E. Mindis, A. Pfaltz, L. Macko, M. Neuberger, M. Zehnder, H. Rüegger and P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265 and refs. cited therein. For the use of chiral, sulphur-containing chelating ligands in Pd-allyl chemistry, see; (c) J. V. Allen, J. F. Bower, J. M. J. Williams, Tetrahedron: Asymmetry 1994, 5, 1895. (d) J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin, J. M. J. Williams, J. Chem. Soc. Perkin Trans. I 1994, 2065. (e) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 55, 1523.
18. For a review, see: (a) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089. For leading references see (b) P. von Matt, G. C. Lloyd-Jones, A.B.E. Mindis, A. Pfaltz, L. Macko, M. Neuberger, M. Zehnder, H. Rüegger and P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265 and refs. cited therein. For the use of chiral, sulphur-containing chelating ligands in Pd-allyl chemistry, see; (c) J. V. Allen, J. F. Bower, J. M. J. Williams, Tetrahedron: Asymmetry 1994, 5, 1895. (d) J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin, J. M. J. Williams, J. Chem. Soc. Perkin Trans. I 1994, 2065. (e) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 55, 1523.
19. For a review, see: (a) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089. For leading references see (b) P. von Matt, G. C. Lloyd-Jones, A.B.E. Mindis, A. Pfaltz, L. Macko, M. Neuberger, M. Zehnder, H. Rüegger and P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265 and refs. cited therein. For the use of chiral, sulphur-containing chelating ligands in Pd-allyl chemistry, see; (c) J. V. Allen, J. F. Bower, J. M. J. Williams, Tetrahedron: Asymmetry 1994, 5, 1895. (d) J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin, J. M. J. Williams, J. Chem. Soc. Perkin Trans. I 1994, 2065. (e) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 55, 1523.
20. (a) T. Hayashi in Ferrocenes, Homogeneous Catalysis, Organic Synthesis, Materials Science, Eds. A. Togni and T. Hayashi, Chapter 2, P. 105, VCH press, Weinheim, 1995 and references therein.
21. (b) M. Sawamura, Y. Ito, Chem. Rev. 1992, 92, 857.
22. A similar conformation was found for thiolate 1 coordinated to Cu(I), see ref. 4a).