Palladium-catalyzed asymmetric phosphination: Enantioselective synthesis of a P-chirogenic phosphine

Journal of the American Chemical Society

Volumn 124, Issue 45, 2002, Pages 13356-13357

  Moncarz, Jillian R ^a   Laritcheva, Natalia F ^a   Glueck, David S ^a  

^a Dartmouth College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PHOSPHINE; PHOSPHORUS;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; TECHNIQUE;

EID: 0037073219     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0267324     Document Type: Article

References (29)

1. (a) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis: The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes, 2nd Ed.; Wiley: New York, 1992.
2. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley-Interscience: New York, 1994.
3. (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411.
4. (b) Kagan, H. B.; Sasaki, M. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley and Sons: Chichester, 1990; Vol. 1, pp 51-102.
5. (a) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.
6. (b) Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950-953.
7. (c) Pd-catalyzed coupling of enantiopure secondary phosphine-boranes with aryl iodides yields tertiary phosphine-boranes in high ee. See: Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776-4778. Oshiki, T.; Imamoto, T. J. Am. Chem. Soc. 1992, 114, 3975-3977.
8. (c) Pd-catalyzed coupling of enantiopure secondary phosphine-boranes with aryl iodides yields tertiary phosphine-boranes in high ee. See: Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776-4778. Oshiki, T.; Imamoto, T. J. Am. Chem. Soc. 1992, 114, 3975-3977.
9. (a) Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748-753.
10. (b) For recent examples, see: Brauer, D. J.; Hingst, M.; Kottsieper, K. W.; Liek, C.; Nickel, T.; Tepper, M.; Stelzer, O.; Sheldrick, W. S. J. Organomet. Chem. 2002, 645, 14-26.
11. Brauer, D. J.; Bitterer, F.; Dorrenbach, F.; Hessler, G.; Stelzer, O.; Kruger, C.; Lutz, F. Z. Naturforsch., B 1996, 51, 1183-1196.
12. Drago, D.; Pregosin, P. S. Organometallics 2002, 21, 1208-1215.
13. Imamoto, T.; Takeyama, T.; Kusumoto, T. Chem. Lett. 1985, 1491-1492.
14. Yamanoi, Y.; Imamoto, T. Rev. Heteroat. Chem. 1999, 20, 227-248.
15. Maienza, F.; Spindler, F.; Thommen, M.; Pugin, B.; Mezzetti, A. J. Org. Chem. 2002, 67, 5239-5249.
16. (a) Roberts, N. K.; Wild, S. B. J. Am. Chem. Soc. 1979, 101, 6254-6260.
17. (b) Wild, S. B. Coord. Chem. Rev. 1997, 166, 291-311. We have not established the absolute configuration of 2; a single enantiomer is shown for convenience.
18. 2) is inconvenient.
19. Using a stoichiometric amount of PH(Me)(Is) yields a 1:1 mixture of diastereomers of 4. Heating this material in THF, or use of excess phosphine in the original synthesis, gives 4 in 1:1.4 ratio.
20. -, which could displace iodide from 3.
21. (a) Wicht, D. K.; Glueck, D. S.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1999, 18, 5130-5140.
22. (b) Wicht, D. K.; Kovacik, I.; Glueck, D. S.; Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141-5151.
23. (c) Zhuravel, M. A.; Glueck, D. S.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2002, 21, 3208-3214.
24. Complex 6 was generated free of 5 by running catalysis with a substoichiometric amount of PhI, or by addition of excess PH(Me)(Is) to Pd(Me-Duphos)(trans-stilbene), At -40 °C, phosphine exchange in 6 is slow on the NMR time scale, and the expected mixture of four diastereomers was observed.
25. Reaction mixtures with PhOTf contain 1 equiv of NaI per Pd, derived from precursor 3. Independent generation of Pd(Me-Duphos)(Ph)(OTf) (from Pd(Me-Duphos)(trans-stilbene) and PhOTf) in the presence of NaI gave 3, consistent with the observations in the catalytic system.
26. Alcazar-Roman, L. M.; Hartwig, J. F. Organometallics 2002, 21, 491-502.
27. Halpern, J. Science 1982, 217, 401-407.
28. Seeman, J. R. Chem. Rev. 1983, 83, 83-134.
29. 3] (1, 2, 3, or 10 equiv of the base per PH(Me)(Is)).