Chiral mixed phosphorus/sulfur ligands for palladium-catalyzed allylic alkylations and aminations

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 2994-2995

  Evans, David A ^a   Campos, Kevin R ^a   Tedrow, Jason S ^a   Michael, Forrest E ^a   Gagné, Michel R ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORUS; SULFUR;

ALKYLATION; AMINATION; ARTICLE; BINDING AFFINITY; CATALYSIS; CHIRALITY; ENANTIOMER; LIGAND BINDING; SYNTHESIS;

EID: 0033617173     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990344b     Document Type: Article

References (31)

1. Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590.
2. (a) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335-422.
3. (b) Murray, S.; Hartley, F. Chem. Rev. 1981, 81, 365-414.
4. Chiral P,N ligands: (a) Pfaltz, A. Acta Chim. Scand. 1996, 50, 189-194 and references therein. (b) Kudis, S.: Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050. (c) Dawson, G. J.; Frost, G.; Williams, J. M. J. Tetrahedron Lett., 1993, 34, 3149-3150.
5. Chiral P,N ligands: (a) Pfaltz, A. Acta Chim. Scand. 1996, 50, 189- 194 and references therein. (b) Kudis, S.: Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050. (c) Dawson, G. J.; Frost, G.; Williams, J. M. J. Tetrahedron Lett., 1993, 34, 3149-3150.
6. Chiral P,N ligands: (a) Pfaltz, A. Acta Chim. Scand. 1996, 50, 189- 194 and references therein. (b) Kudis, S.: Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050. (c) Dawson, G. J.; Frost, G.; Williams, J. M. J. Tetrahedron Lett., 1993, 34, 3149-3150.
7. Chiral N,S ligands: (a) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (b) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753-756. (c) Sprinz, J.; Keifer, M.; Helmchen, G.; Regglein, M.; Huttner, G.; Walter, O.; Zsolanai, L. Tetrahedron Lett. 1994, 10, 1523-1526. (d) Allen, J.; Bower, J.; Williams, J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (e) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. Chiral P,S ligands: (f) Albinati, A.; Pregosin, P.; Wick, K. Organometallics 1996, 15, 2419-2421 and references therein. (g) Hiroi, K.; Suzuki, Y. Tetrahedron Lett. 1998, 39, 6499-6502. (h) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982.
8. Chiral N,S ligands: (a) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (b) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753-756. (c) Sprinz, J.; Keifer, M.; Helmchen, G.; Regglein, M.; Huttner, G.; Walter, O.; Zsolanai, L. Tetrahedron Lett. 1994, 10, 1523-1526. (d) Allen, J.; Bower, J.; Williams, J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (e) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. Chiral P,S ligands: (f) Albinati, A.; Pregosin, P.; Wick, K. Organometallics 1996, 15, 2419-2421 and references therein. (g) Hiroi, K.; Suzuki, Y. Tetrahedron Lett. 1998, 39, 6499-6502. (h) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982.
9. Chiral N,S ligands: (a) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (b) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753-756. (c) Sprinz, J.; Keifer, M.; Helmchen, G.; Regglein, M.; Huttner, G.; Walter, O.; Zsolanai, L. Tetrahedron Lett. 1994, 10, 1523-1526. (d) Allen, J.; Bower, J.; Williams, J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (e) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. Chiral P,S ligands: (f) Albinati, A.; Pregosin, P.; Wick, K. Organometallics 1996, 15, 2419-2421 and references therein. (g) Hiroi, K.; Suzuki, Y. Tetrahedron Lett. 1998, 39, 6499-6502. (h) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982.
10. Chiral N,S ligands: (a) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (b) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753-756. (c) Sprinz, J.; Keifer, M.; Helmchen, G.; Regglein, M.; Huttner, G.; Walter, O.; Zsolanai, L. Tetrahedron Lett. 1994, 10, 1523-1526. (d) Allen, J.; Bower, J.; Williams, J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (e) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. Chiral P,S ligands: (f) Albinati, A.; Pregosin, P.; Wick, K. Organometallics 1996, 15, 2419-2421 and references therein. (g) Hiroi, K.; Suzuki, Y. Tetrahedron Lett. 1998, 39, 6499-6502. (h) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982.
11. Chiral N,S ligands: (a) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (b) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753-756. (c) Sprinz, J.; Keifer, M.; Helmchen, G.; Regglein, M.; Huttner, G.; Walter, O.; Zsolanai, L. Tetrahedron Lett. 1994, 10, 1523-1526. (d) Allen, J.; Bower, J.; Williams, J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (e) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. Chiral P,S ligands: (f) Albinati, A.; Pregosin, P.; Wick, K. Organometallics 1996, 15, 2419-2421 and references therein. (g) Hiroi, K.; Suzuki, Y. Tetrahedron Lett. 1998, 39, 6499-6502. (h) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982.
12. Chiral N,S ligands: (a) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (b) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753-756. (c) Sprinz, J.; Keifer, M.; Helmchen, G.; Regglein, M.; Huttner, G.; Walter, O.; Zsolanai, L. Tetrahedron Lett. 1994, 10, 1523-1526. (d) Allen, J.; Bower, J.; Williams, J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (e) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. Chiral P,S ligands: (f) Albinati, A.; Pregosin, P.; Wick, K. Organometallics 1996, 15, 2419-2421 and references therein. (g) Hiroi, K.; Suzuki, Y. Tetrahedron Lett. 1998, 39, 6499-6502. (h) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982.
13. Chiral N,S ligands: (a) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (b) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753-756. (c) Sprinz, J.; Keifer, M.; Helmchen, G.; Regglein, M.; Huttner, G.; Walter, O.; Zsolanai, L. Tetrahedron Lett. 1994, 10, 1523-1526. (d) Allen, J.; Bower, J.; Williams, J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (e) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. Chiral P,S ligands: (f) Albinati, A.; Pregosin, P.; Wick, K. Organometallics 1996, 15, 2419-2421 and references therein. (g) Hiroi, K.; Suzuki, Y. Tetrahedron Lett. 1998, 39, 6499-6502. (h) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982.
14. Chiral N,S ligands: (a) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (b) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753-756. (c) Sprinz, J.; Keifer, M.; Helmchen, G.; Regglein, M.; Huttner, G.; Walter, O.; Zsolanai, L. Tetrahedron Lett. 1994, 10, 1523-1526. (d) Allen, J.; Bower, J.; Williams, J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (e) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. Chiral P,S ligands: (f) Albinati, A.; Pregosin, P.; Wick, K. Organometallics 1996, 15, 2419-2421 and references therein. (g) Hiroi, K.; Suzuki, Y. Tetrahedron Lett. 1998, 39, 6499-6502. (h) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982.
15. Abel, E.; Bhargava, S. K.; Orrell, K. G. Prog. Inorg. Chem. 1984, 32, 1-118. Abel, E.; Dormer, J.; Ellis, D.; Orrell, K. G.; Sik, V.; Hursthouse, M. B.; Mazid, M. A. J. Chem. Soc., Dalton Trans. 1992, 1073-1080.
16. Abel, E.; Bhargava, S. K.; Orrell, K. G. Prog. Inorg. Chem. 1984, 32, 1-118. Abel, E.; Dormer, J.; Ellis, D.; Orrell, K. G.; Sik, V.; Hursthouse, M. B.; Mazid, M. A. J. Chem. Soc., Dalton Trans. 1992, 1073-1080.
17. For a general review of the asymmetric transition metal-catalyzed allylic alkylation, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422 and references therein.
18. (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145.
19. (b) Nomura, N.; Mennet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745-746 and refs. cited therein.
20. (c) Seebach, D.; Devaquet, E.; Ernst, A.; Hayakawa, M.; Kuhnle, F.; Schweizer, W. B.; Weber, B. Helv. Chim. Acta 1995, 78, 1636-1650.
21. 2Ph (63% ee), Bn (89% ee), Cy (91% ee), tert-butyl (91% ee). See the Supporting Information for the ligand synthesis.
22. 2Ph (93% ee), 4-MeOPh (82% ee), 4-FPh (93% ee), 2-MeOPh (29% ee), Cy (47% ee), and α-naphthyl (30% ee). See the Supporting Information for the ligand synthesis.
23. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145.
24. Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783-4784.
25. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090. Sennhenn, P.; Gabler, B.; Helmchen, G. Tetrahedron Lett. 1994, 35, 8595- 8598. Knuhl, G.; Sennhenn, P.; Heimchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846.
26. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090. Sennhenn, P.; Gabler, B.; Helmchen, G. Tetrahedron Lett. 1994, 35, 8595-8598. Knuhl, G.; Sennhenn, P.; Heimchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846.
27. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090. Sennhenn, P.; Gabler, B.; Helmchen, G. Tetrahedron Lett. 1994, 35, 8595- 8598. Knuhl, G.; Sennhenn, P.; Heimchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846.
28. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050.
29. 3; Z = 4; R = 0.0386, GoF = 0.974.
30. 3; Z = 4; R = 0.0433, GoF = 1.282.
31. The direction of attack trans to the stronger π-acceptor has been previously documented by others: ref 3. See also: Ward, T. R. Organometallics 1996, 15, 2836-2838.