Stereospecific nucleophilic substitution of optically pure H-phosphinates: A general way for the preparation of chiral P-stereogenic phosphine oxides

Journal of the American Chemical Society

Volumn 130, Issue 38, 2008, Pages 12648-12655

  Xu, Qing ^a   Zhao, Chang Qiu ^a   Han, Li Biao ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EPIMERIZATION; NUCLEOPHILIC SUBSTITUTIONS; PHOSPHINATES; PHOSPHINE OXIDES;

PHOSPHORUS COMPOUNDS;

ALKYL GROUP; CHLOROFORM; GRIGNARD REAGENT; LITHIUM DERIVATIVE; NAPHTHALENE DERIVATIVE; ORGANIC COMPOUND; PHENYL GROUP; PHOSPHINE OXIDE DERIVATIVE; PHOSPHORUS; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLIZATION; EPIMERIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LOW TEMPERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; QUANTUM YIELD; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 52449134875     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804412k     Document Type: Article

References (69)

1. (a) Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley-Interscience: New York, 2000.
2. (b) Sasaki, M. In Chirality in Agrochemicals; Kurihara, N., Miyamoto, J., Eds.; Wiley & Sons: Chichester, U.K. 1998; pp 85.
3. (c) Imamoto, T. In Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992; Chapter 1.
4. (d) Crepy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1.
5. (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513.
6. (b) Bigeault, J.; Giordano, L.; Buono, G. Angew. Chem., Int. Ed. 2005, 44, 4753.
7. (c) Ackermann, L.; Born, R.; Spatz, J. H.; Meyer, D. Angew. Chem., Int. Ed. 2005, 44, 7216.
8. (d) Ackermann, L. Synthesis 2006, 1557.
9. (e) Ackermann, L.; Born, R.; Spatz, J. H.; Althammer, A.; Gschrei, C. J. Pure Appl. Chem. 2006, 78, 209.
10. (a) Dubrovina, N. V.; Börner, A. Angew. Chem., Int. Ed. 2004, 43, 5883.
11. (b) Jiang, X.; Minnaard, A. J.; Hessen, B.; Feringa, B. L.; Duchateau, A. L. L.; Andrien, J. G. O.; Boogers, J. A. F.; de Vries, J. G. Org. Lett. 2003, 5, 1503.
12. (c) Dai, W. M.; Yeung, K. K. Y.; Leung, W. H.; Haynes, R. K. Tetrahedron: Asymmetry 2003, 14, 2821.
13. (d) Chan, E. Y. Y.; Zhang, Q.-F.; Sau, Y.-K.; Lo, S. M. F.; Sung, H. H. Y.; Williams, I. D.; Haynes, R. K.; Leung, W. H. Inorg. Chem. 2004, 43, 4921.
14. (e) Nemoto, T.; Jin, L.; Nakamura, H.; Hamada, Y. Tetrahedron Lett. 2006, 47, 6577.
15. (f) Jiang, X.; van den Berg, M.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. Tetrahedron: Asymmetry 2004, 15, 2223.
16. (g) Jiang, X.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. J. Org. Chem. 2004, 69, 2327.
17. Recent preparation of optically active SPOs: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375.
18. (b) Haynes, R. K.; Au-Yeung, T.-L.; Chan, W.-K.; Lam, W.-L.; Li, Z.-Y.; Yeung, L.-Y.; Chan, A. S. C.; Li, P.; Koen, M.; Mitchell, C. R.; Vonwiller, S. C. Eur. J. Org. Chem. 2000, 3205.
19. (c) Haynes, R. K.; Free Man, R. N.; Mitchell, C. R.; Vonwiller, S. C. J. Org. Chem. 1994, 59, 2919.
20. (d) Wang, F.; Polavarapu, P. L.; Drabowicz, J.; Mikolajczyk, M. J. Org. Chem. 2000, 65, 7561.
21. (e) Drabowicz, J.; Lyzwa, P.; Omelanczuk, J.; Pietrusiewicz, K. M.; Mikolajczyk, M. Tetrahedron: Asymmetry, 1999, 10, 2757.
22. (f) Leyris, A.; Nuel, D.; Giordano, L.; Achard, M.; Buono, G. Tetrahedron Lett. 2005, 46, 8677.
23. Xu, Q.; Han, L.-B. Org. Lett. 2006, 8, 2099.
24. (a) Han, L.-B.; Zhao, C.-Q.; Onozawa, S.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842.
25. (b) Han, L.-B.; Zhao, C.-Q. J. Org. Chem. 2005, 70, 10121.
26. (a) A general review: Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley-Interscience: New York, 1972; Vol. 3,Chapter 6.
27. See also: (b) Hays, H. R. J. Org. Chem. 1968, 33, 3690.
28. (c) Grim, S. O.; Satek, L. C. J. Inorg. Nucl. Chem. 1977, 39, 499.
29. (d) Williams, R. H.; Hamilton, L. A. J. Am. Chem. Soc. 1952, 74, 5418.
30. Optically pure H-phosphinates 1a-d can be purchased from Katayama Chemical Industries Co.Ltd. (http://www.katayamakagaku.co.jp). Preparation of optically active H-phosphinates: (a) Farnham, W. B.; Murray, R. K.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 5809.
31. (b) Reiff, L. P.; Aaron, H. S. J. Am. Chem. Soc. 1970, 92, 5275.
32. (c) Benschop, H. P.; Platenburg, D. H. J. M.; Meppelder, F. H.; Boter, H. J. Chem. Commun. 1970, 33.
33. (d) Bodalski, R.; Koszuk, J. Phosphorus, Sulfur, Silicon Relat. Elem. 1989, 44, 99.
34. (e) Reference 6.
35. Early attempts to prepare chiral SPOs via similar substitution reactions only led to the nonselective formation of racemates, see: (a) Emmick, T. L.; Letsinger, R. L. J. Am. Chem. Soc. 1968, 90, 3459.
36. (b) Farnham, W. B.; Murray, R. K.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 5808.
37. (c) Reference 8b.
38. Han, L.-B.; Xu, Q. Japanese Patent JP2008-69103A (filed, 25 August 2006; opened, 3 March2008).
39. (a) Leyris, A.; Bigeault, J.; Nuel, D.; Giordano, L.; Buono, G. Tetrahedron Lett. 2007, 48, 5247.
40. (b) Moraleda, D.; Gatineau, D.; Martin, D.; Giordano, L.; Buono, G. Chem. Commun. 2008, 3031.
41. Other early attempts to obtain chiral SPOs by reduction of the corresponding optically active P-stereogenic precursors using aluminium reagents also failed, see: (a) Reference 9a.
42. (b) Henson, P. D.; Ockrymiek, S. B.; Markham, R. E., Jr. J. Org. Chem. 1974, 39, 2296.
43. (c) Wetzel, R. B.; Kenyon, G. L. J. Org. Chem. 1974, 39, 1531.
44. It was also reported that phosphine oxides undergo rapid stereomutation in the presence of aluminium reagents prior to reduction, see: (d) Henson, P. D.; Nauman, K.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 5645.
45. (e) Reference 9b.
46. (a) Chen, W.-P.; Xiao, J.-L. Tetrahedron Lett. 2001, 42, 2897.
47. (b) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1997, 62, 8560.
48. We found that although stable under basic conditions, 2a instantly epimerizes when treated with diluted hydrogen chloride acid. Even a trace amount of acid can cause this epimerization even at-80°C. Thus, all glasswares used for keeping this compound were all carefully deacidified by washing them first with an alkaline solution and then with water.
49. P)-1a used was recovered without epimerization.
50. (a) Hiiro, T.; Kambe, N.; Ogawa, A.; Miyoshi, N.; Sonoda, N. Angew. Chem., Int. Ed. 1987, 26, 1187.
51. (b) Hiiro, T.; Morita, Y.; Inoue, T.; Kambe, N.; Ogawa, A.; Ryu, I.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 455.
52. (c) Hiiro, T.; Atarashi, Y.; Kambe, N.; Fujiwara, S.; Ogawa, A.; Ryu, I.; Sonoda, N. Organometallics 1990, 9, 1355.
53. (d) Kambe, N.; Inoue, T.; Takeda, T.; Fujiwara, S.-i.; Sonoda, N. J. Am. Chem. Soc. 2006, 128, 12650.
54. See Supporting Information for a table with chemical structures of the products.
55. (a) Moriyama, M. J. Synth. Org. Chem. 1985, 42, 75.
56. (b) Zhang, J.; Xu, Y.; Huang, G.; Guo, H. Tetrahedron Lett. 1988, 29, 1955.
57. (c) Drabowicz, J.; Dudzinski, B.; Mikolajczyk, M. Tetrahedron: Asymmetry 1992, 3, 1231.
58. (d) Omelanczuk, J.; Mikolajczyk, M. Tetrahedron: Asymmetry 1996, 7, 2687.
59. (e) Drabowicz, J.; Dudzinski, B.; Mikolajczyk, M.; Colonna, S.; Gaggero, N. Tetrahedron: Asymmetry 1997, 8, 2267.
60. (f) Drescher, M.; Felsinger, S.; Hammerschmidt, F.; Kählig, H.; Schmidt, S.; Wuggenig, F. Phosphorus, Sulfur, Silicon Relat. Elem. 1998, 140, 79.
61. Kyba, E. P. J. Am. Chem. Soc. 1976, 98, 4805.
62. (a) Haynes, R. K.; Lam, W. W.-L.; Yeung, L.-L. Tetrahedron Lett. 1996, 37, 4729.
63. (b) Lam, W. W.-L.; Haynes, R. K.; Yeung, L.-L.; Chan, E. W.-K. Tetrahedron Lett. 1996, 37, 4733.
64. (c) Haynes, R. K.; Lam, W. W.-L.; Williams, I. D.; Yeung, L.-L. Chem. - Eur. J. 1997, 3, 2052.
65. (d) Au-Yrung, T.-L.; Chan, K.-Y.; Chan, W.-K.; Haynes, R. K.; Williams, I. D.; Yeung, L.-L. Tetrahedron Lett. 2001, 42, 453.
66. (a) Michalski, J.; Skrzypczyński, Z. J. Organomet. Chem. 1975, 97, C31.
67. (b) Krawiecka, B.; Michalski, J.; Wonjna-Tadeusiak, E. J. Org. Chem. 1986, 51, 4201.
68. P)- 1a by t-BuONa and EtOMgCl were also noted (ref 6b).
69. P)-5a with n-BuLi at low temperature indicated that this substitution took place with inversion of configuration at phosphorus via a similar mechanism for phosphites: Neuffer, J.; Richter, W. J. J. Organomet. Chem. 1986, 301, 289.