Synthesis, properties, and reactions of enantiomerically pure, chiral fluorous phosphines of the formula (menthyl)P(CH2CH2(CF2)(n-1)CF3)2 (n=6, 8)

Tetrahedron Asymmetry

Volumn 10, Issue 14, 1999, Pages 2665-2674

  Klose, Alain ^a,b   Gladysz, J A ^a,b  

^a UNIVERSITY OF UTAH   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

METAL DERIVATIVE; PHOSPHINE DERIVATIVE; TERPENE; TOLUENE;

ARTICLE; CHIRALITY; ENANTIOMER; FLUORINATION; PARTITION COEFFICIENT; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033575358     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00272-4     Document Type: Article

References (55)

1. Representative references: (a) Hutchings, G. J. J. Chem. Soc., Chem. Commun. 1999, 301 (mini-review). (b) Pu, L. Chem. Rev. 1998, 98, 2405. (c) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147. (d) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741; Angew. Chem. 1997, 109, 773.
2. Representative references: (a) Hutchings, G. J. J. Chem. Soc., Chem. Commun. 1999, 301 (mini-review). (b) Pu, L. Chem. Rev. 1998, 98, 2405. (c) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147. (d) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741; Angew. Chem. 1997, 109, 773.
3. Representative references: (a) Hutchings, G. J. J. Chem. Soc., Chem. Commun. 1999, 301 (mini-review). (b) Pu, L. Chem. Rev. 1998, 98, 2405. (c) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147. (d) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741; Angew. Chem. 1997, 109, 773.
4. Representative references: (a) Hutchings, G. J. J. Chem. Soc., Chem. Commun. 1999, 301 (mini-review). (b) Pu, L. Chem. Rev. 1998, 98, 2405. (c) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147. (d) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741; Angew. Chem. 1997, 109, 773.
5. Representative references: (a) Hutchings, G. J. J. Chem. Soc., Chem. Commun. 1999, 301 (mini-review). (b) Pu, L. Chem. Rev. 1998, 98, 2405. (c) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147. (d) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741; Angew. Chem. 1997, 109, 773.
6. (a) Horváth, I. T.; Rabái, J. Science 1994, 266, 72.
7. (b) Horváth, I. T.; Kiss, G.; Cook, R. A.; Bond, J. E.; Stevens, P. A.; Rabái, J.; Mozeleski, E. J. J. Am. Chem. Soc. 1998, 120, 3133.
8. (c) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
9. Other reviews: (a) Curran, D. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 1174; Angew. Chem. 1998, 110, 1230. (b) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 37. (c) Barthel-Rosa, L.; Gladysz, J. A. Coord. Chem. Rev. 1999, in press.
10. Other reviews: (a) Curran, D. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 1174; Angew. Chem. 1998, 110, 1230. (b) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 37. (c) Barthel-Rosa, L.; Gladysz, J. A. Coord. Chem. Rev. 1999, in press.
11. Other reviews: (a) Curran, D. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 1174; Angew. Chem. 1998, 110, 1230. (b) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 37. (c) Barthel-Rosa, L.; Gladysz, J. A. Coord. Chem. Rev. 1999, in press.
12. Other reviews: (a) Curran, D. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 1174; Angew. Chem. 1998, 110, 1230. (b) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 37. (c) Barthel-Rosa, L.; Gladysz, J. A. Coord. Chem. Rev. 1999, in press.
13. Alvey, L. J.; Rutherford, D., Juliette, J. J. J.; Gladysz, J. A. J. Org. Chem. 1998, 63, 6302.
14. (a) Juliette, J. J. J.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1610; Angew. Chem. 1997, 109, 1682.
15. (a) Juliette, J. J. J.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1610; Angew. Chem. 1997, 109, 1682.
16. (b) Juliette, J. J. J.; Rutherford, D.; Horváth, I. T.; Gladysz, J. A. J. Am. Chem. Soc. 1999, 121, 2696.
17. (a) Rutherford, D.; Juliette, J. J. J.; Rocaboy, C.; Horváth, I.; Gladysz, J. A. Catalysis Today 1998, 42, 381.
18. (b) Dinh, L.; Gladysz, J. A., manuscript in preparation.
19. This includes the free phosphines: Meier, R. unpublished results, University of Utah and Universität Erlangen-Nürnberg.
20. Throughout this paper, 'menthyl' designates the more readily available 1R,3R,4S (L) enantiomer.
21. (a) Brunner, H.; Janura, M. Synthesis 1998, 45.
22. (b) Stinson, S. C. Chemical & Engineering News 1999, 18 January issue, p. 69 (see: proprietary Heck catalyst, p. 74).
23. Bartik, T.; Ding, H.; Bartik, B.; Hanson, B. E. J. Mol. Catal. A 1995, 98, 117.
24. References to other groups active in the synthesis of fluorous phosphines or metal complexes thereof: (a) Benefice-Malouet, S.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1985, 30, 171. (b) Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P. Tetrahedron: Asymmetry 1997, 8, 715. (c) Battacharyya, P.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Stuart, A. M. J. Chem. Soc., Perkin Trans. 1 1997, 3609. (d) Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1628; Angew. Chem. 1997, 109, 1699. (e) Haar, C. M.; Huang, J.; Nolan, S. P.; Peterson, J. L. Organometallics 1998, 17, 5018. (f) Mathivet, T.; Monflier, E.; Castanet, Y.; Montreux, A.; Couturier, J.-L. Tetrahedron Lett. 1998, 39, 9411. (g) Fawcett, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russell, D. R.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3751. (h) Hope, E. G.; Kemmitt, R. D. W.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3765.
25. References to other groups active in the synthesis of fluorous phosphines or metal complexes thereof: (a) Benefice- Malouet, S.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1985, 30, 171. (b) Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P. Tetrahedron: Asymmetry 1997, 8, 715. (c) Battacharyya, P.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Stuart, A. M. J. Chem. Soc., Perkin Trans. 1 1997, 3609. (d) Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1628; Angew. Chem. 1997, 109, 1699. (e) Haar, C. M.; Huang, J.; Nolan, S. P.; Peterson, J. L. Organometallics 1998, 17, 5018. (f) Mathivet, T.; Monflier, E.; Castanet, Y.; Montreux, A.; Couturier, J.-L. Tetrahedron Lett. 1998, 39, 9411. (g) Fawcett, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russell, D. R.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3751. (h) Hope, E. G.; Kemmitt, R. D. W.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3765.
26. References to other groups active in the synthesis of fluorous phosphines or metal complexes thereof: (a) Benefice- Malouet, S.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1985, 30, 171. (b) Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P. Tetrahedron: Asymmetry 1997, 8, 715. (c) Battacharyya, P.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Stuart, A. M. J. Chem. Soc., Perkin Trans. 1 1997, 3609. (d) Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1628; Angew. Chem. 1997, 109, 1699. (e) Haar, C. M.; Huang, J.; Nolan, S. P.; Peterson, J. L. Organometallics 1998, 17, 5018. (f) Mathivet, T.; Monflier, E.; Castanet, Y.; Montreux, A.; Couturier, J.-L. Tetrahedron Lett. 1998, 39, 9411. (g) Fawcett, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russell, D. R.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3751. (h) Hope, E. G.; Kemmitt, R. D. W.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3765.
27. References to other groups active in the synthesis of fluorous phosphines or metal complexes thereof: (a) Benefice- Malouet, S.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1985, 30, 171. (b) Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P. Tetrahedron: Asymmetry 1997, 8, 715. (c) Battacharyya, P.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Stuart, A. M. J. Chem. Soc., Perkin Trans. 1 1997, 3609. (d) Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1628; Angew. Chem. 1997, 109, 1699. (e) Haar, C. M.; Huang, J.; Nolan, S. P.; Peterson, J. L. Organometallics 1998, 17, 5018. (f) Mathivet, T.; Monflier, E.; Castanet, Y.; Montreux, A.; Couturier, J.-L. Tetrahedron Lett. 1998, 39, 9411. (g) Fawcett, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russell, D. R.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3751. (h) Hope, E. G.; Kemmitt, R. D. W.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3765.
28. References to other groups active in the synthesis of fluorous phosphines or metal complexes thereof: (a) Benefice- Malouet, S.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1985, 30, 171. (b) Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P. Tetrahedron: Asymmetry 1997, 8, 715. (c) Battacharyya, P.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Stuart, A. M. J. Chem. Soc., Perkin Trans. 1 1997, 3609. (d) Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1628; Angew. Chem. 1997, 109, 1699. (e) Haar, C. M.; Huang, J.; Nolan, S. P.; Peterson, J. L. Organometallics 1998, 17, 5018. (f) Mathivet, T.; Monflier, E.; Castanet, Y.; Montreux, A.; Couturier, J.-L. Tetrahedron Lett. 1998, 39, 9411. (g) Fawcett, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russell, D. R.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3751. (h) Hope, E. G.; Kemmitt, R. D. W.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3765.
29. References to other groups active in the synthesis of fluorous phosphines or metal complexes thereof: (a) Benefice- Malouet, S.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1985, 30, 171. (b) Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P. Tetrahedron: Asymmetry 1997, 8, 715. (c) Battacharyya, P.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Stuart, A. M. J. Chem. Soc., Perkin Trans. 1 1997, 3609. (d) Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1628; Angew. Chem. 1997, 109, 1699. (e) Haar, C. M.; Huang, J.; Nolan, S. P.; Peterson, J. L. Organometallics 1998, 17, 5018. (f) Mathivet, T.; Monflier, E.; Castanet, Y.; Montreux, A.; Couturier, J.-L. Tetrahedron Lett. 1998, 39, 9411. (g) Fawcett, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russell, D. R.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3751. (h) Hope, E. G.; Kemmitt, R. D. W.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3765.
30. References to other groups active in the synthesis of fluorous phosphines or metal complexes thereof: (a) Benefice- Malouet, S.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1985, 30, 171. (b) Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P. Tetrahedron: Asymmetry 1997, 8, 715. (c) Battacharyya, P.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Stuart, A. M. J. Chem. Soc., Perkin Trans. 1 1997, 3609. (d) Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1628; Angew. Chem. 1997, 109, 1699. (e) Haar, C. M.; Huang, J.; Nolan, S. P.; Peterson, J. L. Organometallics 1998, 17, 5018. (f) Mathivet, T.; Monflier, E.; Castanet, Y.; Montreux, A.; Couturier, J.-L. Tetrahedron Lett. 1998, 39, 9411. (g) Fawcett, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russell, D. R.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3751. (h) Hope, E. G.; Kemmitt, R. D. W.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3765.
31. References to other groups active in the synthesis of fluorous phosphines or metal complexes thereof: (a) Benefice- Malouet, S.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1985, 30, 171. (b) Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P. Tetrahedron: Asymmetry 1997, 8, 715. (c) Battacharyya, P.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Stuart, A. M. J. Chem. Soc., Perkin Trans. 1 1997, 3609. (d) Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1628; Angew. Chem. 1997, 109, 1699. (e) Haar, C. M.; Huang, J.; Nolan, S. P.; Peterson, J. L. Organometallics 1998, 17, 5018. (f) Mathivet, T.; Monflier, E.; Castanet, Y.; Montreux, A.; Couturier, J.-L. Tetrahedron Lett. 1998, 39, 9411. (g) Fawcett, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russell, D. R.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3751. (h) Hope, E. G.; Kemmitt, R. D. W.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3765.
32. References to other groups active in the synthesis of fluorous phosphines or metal complexes thereof: (a) Benefice- Malouet, S.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1985, 30, 171. (b) Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P. Tetrahedron: Asymmetry 1997, 8, 715. (c) Battacharyya, P.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Stuart, A. M. J. Chem. Soc., Perkin Trans. 1 1997, 3609. (d) Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1628; Angew. Chem. 1997, 109, 1699. (e) Haar, C. M.; Huang, J.; Nolan, S. P.; Peterson, J. L. Organometallics 1998, 17, 5018. (f) Mathivet, T.; Monflier, E.; Castanet, Y.; Montreux, A.; Couturier, J.-L. Tetrahedron Lett. 1998, 39, 9411. (g) Fawcett, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Russell, D. R.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3751. (h) Hope, E. G.; Kemmitt, R. D. W.; Stuart, A. M. J. Chem. Soc., Dalton Trans. 1998, 3765.
33. Sinou, D.; Pozzi, G.; Hope, E. G.; Stuart, A. M. Tetrahedron Lett. 1999, 40, 849.
34. Pozzi, G.; Cinato, F.; Montanari, F.; Quici, S. J. Chem. Soc., Chem. Commun. 1998, 877.
35. (a) Hinke, A.; Kuchen, W. Phosphorus and Sulfur 1983, 15, 93.
36. (b) Detailed NMR assignments: Feigel, M.; Haegele, G.; Hinke, A.; Tossing, G. Z. Naturforsch. 1982, 37b, 1661.
37. Marinetti, A.; Buzin, F. X.; Ricard, L. Tetrahedron 1997, 53, 4363.
38. Valentine Jr., D.; Blount, J. F.; Toth, K. J. Org. Chem. 1980, 45, 3691.
39. Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450.
40. f6 as a by-product: Kainz, S.; Luo, Z.; Curran, D. P.; Leitner, W. Synthesis 1998, 1425.
41. (a) Hidai, M.; Mizuta, H.; Yagi, H.; Nagai, Y.; Hata, K.; Uchida, Y. J. Organomet. Chem. 1982, 232, 89.
42. (b) Tanaka, M.; Ogata, I. Bull. Chem. Soc. Jpn. 1975, 48, 1094.
43. Guillevic, M.-A.; Rocaboy, C.; Arif, A. M.; Horváth, I. T.; Gladysz, J. A. Organometallics 1998, 17, 707.
44. Alvey, L. J. PhD Thesis, University of Utah, 1999.
45. (a) Crabtree, R. H.; Gautier, A.; Giordano, G.; Khan, T. J. Organomet. Chem. 1977, 141, 113.
46. (b) Denise, B.; Pannetier, G. J. Organomet. Chem. 1978, 148, 155.
47. (c) Petrucci-Samija, M.; Guillemette, V.; Dasgupta, M.; Kakar, A. K. J. Am. Chem. Soc. 1999, 121, 1968.
48. Dewey, M. A.; Gladysz, J. A. Organometallics 1993, 12, 2390.
49. Smith, J. G.; Wright, G. F. J. Org. Chem. 1952, 17, 1116.
50. Krause, H. W.; Kinting, A. J. Prakt. Chem. 1980, 3, 485.
51. 11c Important details regarding this sequence are described in the text.
52. 17
53. fn groups are diastereotopic.
54. 25
55. 2, 100), 485 (45), 441 (40), 427 (15), 395 (24), 377 (92); no other peaks above 200 of >15%.