Pt(Me-Duphos)-catalyzed asymmetric hydrophosphination of activated olefins: Enantioselective synthesis of chiral phosphines

Organometallics

Volumn 19, Issue 6, 2000, Pages 950-953

  Kovacik, Ivan ^a   Wicht, Denyce K ^a   Grewal, Navrose S ^a   Glueck, David S ^a   Incarvito, Christopher D ^b   Guzei, Ilia A ^b   Rheingold, Arnold L ^b  

^a Dartmouth College   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001148561     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990882e     Document Type: Article

References (32)

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5. An important recent exception is Burk's synthesis of Duphos ligands, which relies on Ru-Binap-catalyzed asymmetric hydrogenation of β-keto esters (Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Sac. 1993, 115, 10125-10138).
6. Pringle and co-workers have shown that Pt-catalyzed hydrophosphination can be used to prepare functionalized phosphines. (a) Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49-50. (b) Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277-4282. (c) Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Kluwer: Dordrecht, 1995; Vol. 5; pp 111-122. (d) Hoye, P. A. T.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1993, 74, 269-274. (e) Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701-1702. (f) Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1989, 1096-1097. See also: (g) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (h) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51.
7. Pringle and co-workers have shown that Pt-catalyzed hydrophosphination can be used to prepare functionalized phosphines. (a) Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49-50. (b) Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277-4282. (c) Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Kluwer: Dordrecht, 1995; Vol. 5; pp 111-122. (d) Hoye, P. A. T.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1993, 74, 269-274. (e) Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701-1702. (f) Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1989, 1096-1097. See also: (g) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (h) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51.
8. Pringle and co-workers have shown that Pt-catalyzed hydrophosphination can be used to prepare functionalized phosphines. (a) Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49-50. (b) Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277-4282. (c) Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Kluwer: Dordrecht, 1995; Vol. 5; pp 111-122. (d) Hoye, P. A. T.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1993, 74, 269-274. (e) Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701-1702. (f) Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1989, 1096-1097. See also: (g) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (h) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51.
9. Pringle and co-workers have shown that Pt-catalyzed hydrophosphination can be used to prepare functionalized phosphines. (a) Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49-50. (b) Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277-4282. (c) Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Kluwer: Dordrecht, 1995; Vol. 5; pp 111-122. (d) Hoye, P. A. T.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1993, 74, 269-274. (e) Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701-1702. (f) Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1989, 1096-1097. See also: (g) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (h) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51.
10. Pringle and co-workers have shown that Pt-catalyzed hydrophosphination can be used to prepare functionalized phosphines. (a) Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49-50. (b) Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277-4282. (c) Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Kluwer: Dordrecht, 1995; Vol. 5; pp 111-122. (d) Hoye, P. A. T.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1993, 74, 269-274. (e) Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701-1702. (f) Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1989, 1096-1097. See also: (g) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (h) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51.
11. Pringle and co-workers have shown that Pt-catalyzed hydrophosphination can be used to prepare functionalized phosphines. (a) Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49-50. (b) Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277-4282. (c) Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Kluwer: Dordrecht, 1995; Vol. 5; pp 111-122. (d) Hoye, P. A. T.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1993, 74, 269-274. (e) Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701-1702. (f) Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1989, 1096-1097. See also: (g) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (h) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51.
12. Pringle and co-workers have shown that Pt-catalyzed hydrophosphination can be used to prepare functionalized phosphines. (a) Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49-50. (b) Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277-4282. (c) Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Kluwer: Dordrecht, 1995; Vol. 5; pp 111-122. (d) Hoye, P. A. T.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1993, 74, 269-274. (e) Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701-1702. (f) Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1989, 1096-1097. See also: (g) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (h) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51.
13. Pringle and co-workers have shown that Pt-catalyzed hydrophosphination can be used to prepare functionalized phosphines. (a) Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49-50. (b) Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277-4282. (c) Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Kluwer: Dordrecht, 1995; Vol. 5; pp 111-122. (d) Hoye, P. A. T.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1993, 74, 269-274. (e) Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701-1702. (f) Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1989, 1096-1097. See also: (g) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (h) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; pp 35-51.
14. (a) Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039-5040.
15. (b) Wicht, D. K.; Kourkine, I. V.; Kovacik, I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381-5394.
16. (a) Wicht, D. K.; Glueck, D. S.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1999, 18, 5130-5140.
17. (b) Wicht, D. K.; Kovacik, I.; Glueck, D. S.; Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141-5151.
18. (a) Me-Duphos = (R,R)-Me-Duphos as shown in Figures 1 and 2 and Scheme 4; see: Wicht, D. K.; Zhuravel, M. A.; Gregush, R. V.; Glueck, D. S.; Guzei, I. A.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1998, 17, 1412-1419, for this and other stilbene complexes.
19. 2) = 9.28%.
20. (c) Pt-P distances (Å) for other chiral Pt(diphos)-(trans-stilbene) complexes: for Tol-Binap, 2.2806(9), 2.2840(8); for Chiraphos, 2.272(2), 2.277(2), 2.271(2), 2.274(2); for Diop, 2.284(2), 2.290(2).
21. Brauer, D. J.; Bitterer, F.; Dorrenbach, F.; Hessler, G.; Stelzer, O.; Kruger, C.; Lutz, F. Z. Naturforsch. B 1996, 51, 1183-1196.
22. 3Pt: C, 57.54; H, 7.07. Found: C, 65.62; H, 7.75; an additional sample also gave poor results: C, 51.65; H, 7.00.
23. 2) = 12.05%.
24. 1H NMR hydride signals.
25. 4)(Cl)(L)]. See: (a) Otsuka, S.; Nakamura, A.; Kano, T.; Tani, K. J. Am. Chem. Soc. 1971, 93, 4301-4303. (b) Roberts, N. K.; Wild, S. B. J. Am. Chem. Soc. 1979, 101, 6254-6260. (c) For a review, see: Wild, S. B. Coord. Chem. Rev. 1997, 166, 291-311.
26. 4)(Cl)(L)]. See: (a) Otsuka, S.; Nakamura, A.; Kano, T.; Tani, K. J. Am. Chem. Soc. 1971, 93, 4301-4303. (b) Roberts, N. K.; Wild, S. B. J. Am. Chem. Soc. 1979, 101, 6254-6260. (c) For a review, see: Wild, S. B. Coord. Chem. Rev. 1997, 166, 291-311.
27. 4)(Cl)(L)]. See: (a) Otsuka, S.; Nakamura, A.; Kano, T.; Tani, K. J. Am. Chem. Soc. 1971, 93, 4301-4303. (b) Roberts, N. K.; Wild, S. B. J. Am. Chem. Soc. 1979, 101, 6254-6260. (c) For a review, see: Wild, S. B. Coord. Chem. Rev. 1997, 166, 291-311.
28. Pt-P = 2889). For more spectroscopic data, see the Supporting Information.
29. The relative amounts of these products depended on temperature and reaction time; phosphine 4 was the major organic product, and more PH(Ph)(Is) was formed at higher temperature. See the Supporting Information for additional details.
30. Some of the tertiary phosphine products in Table 2 were reported previously. For entry 2, see ref 5b; for entries 4-6, see: Wolfsberger, W. Chem. Ztg. 1990, 114, 353-354. For entry 10, see: Habib, M.; Trujillo, H.; Alexander, C. A.; Storhoff, B. N. Inorg. Chem. 1985, 24, 2344-2349. For the other phosphines, see the Supporting Information.
31. Some of the tertiary phosphine products in Table 2 were reported previously. For entry 2, see ref 5b; for entries 4-6, see: Wolfsberger, W. Chem. Ztg. 1990, 114, 353-354. For entry 10, see: Habib, M.; Trujillo, H.; Alexander, C. A.; Storhoff, B. N. Inorg. Chem. 1985, 24, 2344-2349. For the other phosphines, see the Supporting Information.
32. Yoshifuji, M.; Shibayama, K.; Inamoto, N. Chem. Lett. 1984, 115-118.