Versatile ligands for palladium-catalyzed asymmetric allylic alkylation

Angewandte Chemie - International Edition

Volumn 37, Issue 22, 1998, Pages 3116-3118

  Dierkes, Peter ^b   Ramdeehul, Shailesh ^a   Barloy, Laurent ^a   De Cian, Andre ^a   Fischer, Jean ^a   Kamer, Paul C J ^b   Van Leeuwen, Piet W N M ^b   Osborn, John A ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Alkylations; Asymmetric catalysis; Chiral ligands; Homogeneous catalysis; Palladium

Indexed keywords

ALLYL COMPOUND; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; DRUG SYNTHESIS; ENANTIOMER; LIGAND BINDING; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 0032484170     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981204)37:22<3116::AID-ANIE3116>3.0.CO;2-S     Document Type: Article

References (29)

1. Reviews: a) B. M. Trost, D. L. van Vranken, Chem. Rev. 1996, 96, 395-422; b) T. Hayashi in Catalytic Asymmetric Synthesis, Vol. 1 (Ed.: I. Ojima), VCH, New York, 1993, pp. 325-365; c) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276.
2. Reviews: a) B. M. Trost, D. L. van Vranken, Chem. Rev. 1996, 96, 395-422; b) T. Hayashi in Catalytic Asymmetric Synthesis, Vol. 1 (Ed.: I. Ojima), VCH, New York, 1993, pp. 325-365; c) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276.
3. Reviews: a) B. M. Trost, D. L. van Vranken, Chem. Rev. 1996, 96, 395-422; b) T. Hayashi in Catalytic Asymmetric Synthesis, Vol. 1 (Ed.: I. Ojima), VCH, New York, 1993, pp. 325-365; c) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276.
4. Reviews: a) B. M. Trost, D. L. van Vranken, Chem. Rev. 1996, 96, 395-422; b) T. Hayashi in Catalytic Asymmetric Synthesis, Vol. 1 (Ed.: I. Ojima), VCH, New York, 1993, pp. 325-365; c) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276.
5. However, see a) G. Knühl, P. Sennhenn, G. Helmchen, J. Chem. Soc. Chem. Commun. 1995, 1845-1846: b) B. M. Trost, A. C. Krueger, R. C. Bunt, J. Zambrano, J. Am. Chem. Soc. 1996, 118, 6520-6521.
6. However, see a) G. Knühl, P. Sennhenn, G. Helmchen, J. Chem. Soc. Chem. Commun. 1995, 1845-1846: b) B. M. Trost, A. C. Krueger, R. C. Bunt, J. Zambrano, J. Am. Chem. Soc. 1996, 118, 6520-6521.
7. Both early and late transition states have been proposed. Early transition states: a) P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054; b) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 35, 1523-1526; c) P. S. Pregosin, R. Salzmann, A. Togni, Organometallics 1995, 14, 842-847; d) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031-1037; late transition states: e) B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3416-3426; f) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506; g) P. von Matt, G. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuburger, M. Zehnder, H. Rüegger, P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265-284; h) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110.
8. Both early and late transition states have been proposed. Early transition states: a) P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054; b) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 35, 1523-1526; c) P. S. Pregosin, R. Salzmann, A. Togni, Organometallics 1995, 14, 842-847; d) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031-1037; late transition states: e) B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3416-3426; f) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506; g) P. von Matt, G. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuburger, M. Zehnder, H. Rüegger, P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265-284; h) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110.
9. Both early and late transition states have been proposed. Early transition states: a) P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054; b) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 35, 1523-1526; c) P. S. Pregosin, R. Salzmann, A. Togni, Organometallics 1995, 14, 842-847; d) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031-1037; late transition states: e) B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3416-3426; f) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506; g) P. von Matt, G. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuburger, M. Zehnder, H. Rüegger, P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265-284; h) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110.
10. Both early and late transition states have been proposed. Early transition states: a) P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054; b) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 35, 1523-1526; c) P. S. Pregosin, R. Salzmann, A. Togni, Organometallics 1995, 14, 842-847; d) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031-1037; late transition states: e) B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3416-3426; f) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506; g) P. von Matt, G. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuburger, M. Zehnder, H. Rüegger, P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265-284; h) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110.
11. Both early and late transition states have been proposed. Early transition states: a) P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054; b) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 35, 1523-1526; c) P. S. Pregosin, R. Salzmann, A. Togni, Organometallics 1995, 14, 842-847; d) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031-1037; late transition states: e) B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3416-3426; f) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506; g) P. von Matt, G. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuburger, M. Zehnder, H. Rüegger, P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265-284; h) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110.
12. Both early and late transition states have been proposed. Early transition states: a) P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054; b) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 35, 1523-1526; c) P. S. Pregosin, R. Salzmann, A. Togni, Organometallics 1995, 14, 842-847; d) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031-1037; late transition states: e) B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3416-3426; f) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506; g) P. von Matt, G. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuburger, M. Zehnder, H. Rüegger, P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265-284; h) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110.
13. Both early and late transition states have been proposed. Early transition states: a) P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054; b) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 35, 1523-1526; c) P. S. Pregosin, R. Salzmann, A. Togni, Organometallics 1995, 14, 842-847; d) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031-1037; late transition states: e) B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3416-3426; f) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506; g) P. von Matt, G. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuburger, M. Zehnder, H. Rüegger, P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265-284; h) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110.
14. Both early and late transition states have been proposed. Early transition states: a) P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054; b) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 35, 1523-1526; c) P. S. Pregosin, R. Salzmann, A. Togni, Organometallics 1995, 14, 842-847; d) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031-1037; late transition states: e) B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3416-3426; f) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506; g) P. von Matt, G. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuburger, M. Zehnder, H. Rüegger, P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265-284; h) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110.
15. Both early and late transition states have been proposed. Early transition states: a) P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054; b) J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, L. Zsolnai, Tetrahedron Lett. 1994, 35, 1523-1526; c) P. S. Pregosin, R. Salzmann, A. Togni, Organometallics 1995, 14, 842-847; d) A. Togni, U. Burckhardt, V. Gramlich, P. S. Pregosin, R. Salzmann, J. Am. Chem. Soc. 1996, 118, 1031-1037; late transition states: e) B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3416-3426; f) J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506; g) P. von Matt, G. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuburger, M. Zehnder, H. Rüegger, P. S. Pregosin, Helv. Chim. Acta 1995, 78, 265-284; h) H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110.
16. a) M. Kranenburg, J. G. P. Delis, P. C. J. Kamer, P. W. N. M. van Leeuwen, K. Vrieze, N. Veldman, A. L. Spek, K. Goubitz, J. Fraanje, J. Chem. Soc. Dalton Trans. 1997, 1839-1849;
17. b) M. Kranenburg, Y. E. M. van der Burgt, P. C. J. Kamer, P. W. N. M. van Leeuwen, Organometallics 1995, 14, 3081-3089;
18. c) M. Kranenburg, P. C. J. Kamer, P. W. N. M. van Leeuwen, Eur. J. Inorg. Chem. 1998, 25-27.
19. M. J. Burk, M. F. Gross, Tetrahedron Lett. 1994, 35, 9363-9366.
20. A ligand derived from the xanthene backbone with chirality at phosphorus was recently reported: Y. Hamada, F. Matsuura, M. Oku, K. Hatano, T. Shioiri, Tetrahedron Lett. 1997, 38, 8961-8964.
21. The configurations of the products were assigned by comparison of their optical rotations with literature data: a) P. Sennhenn, B. Gabler, G. Helmchen, Tetrahedron Lett. 1994, 35, 8595-8598; b) B. M. Trost, A. C. Krueger, R. C. Bunt, J. Zambrano, J. Am. Chem. Soc. 1996, 118, 6520-6521; c) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-616; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568.
22. The configurations of the products were assigned by comparison of their optical rotations with literature data: a) P. Sennhenn, B. Gabler, G. Helmchen, Tetrahedron Lett. 1994, 35, 8595-8598; b) B. M. Trost, A. C. Krueger, R. C. Bunt, J. Zambrano, J. Am. Chem. Soc. 1996, 118, 6520-6521; c) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-616; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568.
23. The configurations of the products were assigned by comparison of their optical rotations with literature data: a) P. Sennhenn, B. Gabler, G. Helmchen, Tetrahedron Lett. 1994, 35, 8595-8598; b) B. M. Trost, A. C. Krueger, R. C. Bunt, J. Zambrano, J. Am. Chem. Soc. 1996, 118, 6520-6521; c) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-616; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568.
24. The configurations of the products were assigned by comparison of their optical rotations with literature data: a) P. Sennhenn, B. Gabler, G. Helmchen, Tetrahedron Lett. 1994, 35, 8595-8598; b) B. M. Trost, A. C. Krueger, R. C. Bunt, J. Zambrano, J. Am. Chem. Soc. 1996, 118, 6520-6521; c) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-616; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568.
25. BSA = N,O-bis(trimethylsilyl)acetamide.
26. -3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101 072. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
27. b) C. K. Fair in MoleN. "An Interactive Intelligent System for Crystal Structure Analysis". Nonius, Delft, The Netherlands, 1990.
28. A SPARTAN computer graphic programme was used, but in view of the approximate nature of these calculations, more detailed studies are in progress.
29. [3f] See also ref. [3d].