Asymmetric organocatalytic electrophilic phosphination

Angewandte Chemie - International Edition

Volumn 50, Issue 14, 2011, Pages 3211-3214

  Nielsen, Martin ^a   Jacobsen, Christian Borch ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

asymmetric synthesis; organocatalysis; phosphorus; synthetic methods

Indexed keywords

ASYMMETRIC SYNTHESIS; BOND FORMATION; CATALYTIC AMOUNTS; CINCHONA ALKALOID; ELECTROPHILES; GOOD YIELD; ONE POT PROCESS; ORGANOCATALYSIS; ORGANOCATALYTIC; REACTION MECHANISM; SYNTHETIC METHODS;

AMINO ACIDS; CATALYSIS; METABOLITES; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS COMPOUNDS; RATE CONSTANTS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

PHOSPHORUS;

EID: 79953014410     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201007188     Document Type: Article

References (89)

1. For a review, see:, S. C. Fields, Tetrahedron 1999, 55, 12237.
2. For a review on the synthesis of phosphorus analogues of α-amino acids, see:, F. Palacios, C. Alonso, J. M. Santos, Chem. Rev. 2005, 105, 899.
3. A. Börner, Phosphorous Ligands in Asymmetric Catalysis: Synthesis and Applications, Wiley-VCH, Weinheim, 2008; for reviews, see
4. D. S. Glueck, Chem. Eur. J. 2008, 14, 7108
5. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029
6. K. V. L. Crépy, T. Imamoto, Top. Curr. Chem. 2003, 229, 1
7. J. I. van-der-Vlugt, J. N. H. Reek, Angew. Chem. 2009, 121, 8990
8. Angew. Chem. Int. Ed. 2009, 48, 8832
9. L. Kollár, G. Keglevich, Chem. Rev. 2010, 110, 4257.
10. For reviews, see
11. G. Adair, S. Mukherjee, B. List, Aldrichimica Acta 2008, 41, 31
12. T. Akiyama, Chem. Rev. 2007, 107, 5744
13. A. C. Spivey, S. Arseniyadis, Top. Curr. Chem. 2009, 291, 233
14. J. L. Methot, W. R. Roush, Adv. Synth. Catal. 2004, 346, 1035; for recent examples, see
15. R. He, X. Wang, T. Hashimoto, K. Maruoka, Angew. Chem. 2008, 120, 9608
16. Angew. Chem. Int. Ed. 2008, 47, 9466
17. R. He, C. Ding, K. Maruoka, Angew. Chem. 2009, 121, 4629
18. Angew. Chem. Int. Ed. 2009, 48, 4559
19. D. Uraguchi, T. Ito, S. Nakamura, T. Ooi, Chem. Sci. 2010, 1, 488.
20. P. Savignac, B. Iorga, Modern Phosphonates Chemistry, CRC, New York, 2003
21. P. J. Murphy, Organophosphorous Reagents, Oxford University Press, Oxford, 2004; for a review on the phospha-Michael addition in organic synthesis, see
22. D. Enders, A. Saint-Dizier, M. I. Lannou, A. Lenzen, Eur. J. Org. Chem. 2006, 29.
23. For reviews, see e.g.
24. K. M. Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375
25. O. I. Kolodiazhnyi, Tetrahedron: Asymmetry 1998, 9, 1279
26. O. Molt, T. Schrader, Synthesis 2002, 2633
27. Ś. Albrecht, A. Albrecht, H. Krawczyk, K. A. Jørgensen, Chem. Eur. J. 2010, 16, 28; for an example see
28. E. Bergin, C. T. O'Connor, S. B. Robinson, E. M. McGarrigle, C. P. O'Mahony, D. G. Gilheany, J. Am. Chem. Soc. 2007, 129, 9566.
29. For examples, see
30. J. J. Feng, X. F. Chen, M. Shi, W. L. Duan, J. Am. Chem. Soc. 2010, 132, 5562
31. P. Butti, R. Rochat, A. D. Sadow, A. Togni, Angew. Chem. 2008, 120, 4956
32. Angew. Chem. Int. Ed. 2008, 47, 4878
33. A. D. Sadow, I. Haller, L. Fadini, A. Togni, J. Am. Chem. Soc. 2004, 126, 14704
34. A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Angew. Chem. 2007, 119, 4588
35. Angew. Chem. Int. Ed. 2007, 46, 4504
36. Y. Zhu, J. P. Malerich, V. H. Rawal, Angew. Chem. 2010, 122, 157
37. Angew. Chem. Int. Ed. 2010, 49, 153
38. M. Terada, T. Ikehara, H. Ube, J. Am. Chem. Soc. 2007, 129, 14112
39. E. Maerten, S. Cabrera, A. Kjærsgaard, K. A. Jørgensen, J. Org. Chem. 2007, 72, 8893
40. I. Ibrahem, R. Rios, J. Vesely, P. Hammer, L. Eriksson, F. Himo, A. Cordova, Angew. Chem. 2007, 119, 4591
41. Angew. Chem. Int. Ed. 2007, 46, 4507.
42. For examples of the use of cyanoacetates in organocatalysis, see
43. S. Saaby, M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 8120
44. H. Li, J. Song, X. Liu, L. Deng, J. Am. Chem. Soc. 2005, 127, 8948
45. X. Wang, M. Kitamura, K. Maruoka, J. Am. Chem. Soc. 2007, 129, 1038
46. S. Santoro, T. B. Poulsen, K. A. Jørgensen, Chem. Commun. 2007, 5155
47. T. B. Poulsen, G. Dickmeiss, J. Overgaard, K. A. Jørgensen, Angew. Chem. 2008, 120, 4765
48. Angew. Chem. Int. Ed. 2008, 47, 4687.
49. For reviews on organocatalysis, see
50. Chem. Rev. 2007, 107, 5413 (issue on organocatalysis)
51. T. Marcelli, H. Hiemstra, Synthesis 2010, 1229.
52. For reviews on β-amino acids, see
53. M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991
54. B. Weiner, W. Szymański, D. B. Janssen, A. J. Minnaard, B. L. Feringa, Chem. Soc. Rev. 2010, 39, 1656.
55. For examples on phase transfer catalyzed reactions producing acid during the course of the reaction, see
56. U. Dolling, P. Davis, E. J. J. Grabowski, J. Am. Chem. Soc. 1984, 106, 446
57. M. J. O'Donnell, W. D. Bennett, S. Wu, J. Am. Chem. Soc. 1989, 111, 2353
58. E. J. Corey, F. Xu, M. Noe, J. Am. Chem. Soc. 1997, 119, 12414
59. T. B. Poulsen, L. Bernardi, M. Bell, K. A. Jørgensen, Angew. Chem. 2006, 118, 6701
60. Angew. Chem. Int. Ed. 2006, 45, 6551.
61. See the Supporting Information.
62. R. W. Alder, P. S. Bowman, W. R. S. Steele, D. R. Winterman, Chem. Commun. 1968, 723.
63. S. Caddick, D. B. Judd, A. K. K. Lewis, M. T. Reich, M. R. V. Williams, Tetrahedron 2003, 59, 5417.
64. CCDC-795889 (4c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
65. For reviews on asymmetric organocatalysis using nucleophilic activators, see
66. M. J. Gaunt, C. C. C. Johansson, Chem. Rev. 2007, 107, 5596
67. E. M. McGarrigle, E. L. Myers, O. Illa, M. A. Shaw, S. L. Riches, V. K. Aggarwal, Chem. Rev. 2007, 107, 5841.
68. For other examples of the formation of salt complexes containing an N-P bond, see
69. C. Lensink, S. K. Xi, L. M. Daniels, J. G. Verkade, J. Am. Chem. Soc. 1989, 111, 3478
70. R. Boomishankar, J. Ledger, J. B. Guilbaud, N. L. Campbell, J. Basca, R. Bonar-Law, Y. Z. Khimyak, A. Steiner, Chem. Commun. 2007, 5152
71. R. Weiss, S. Engel, Synthesis 1991, 1077
72. M. Blättner, M. Nieger, A. Ruban, W. W. Schoeller, E. Niecke, Angew. Chem. 2000, 112, 2876
73. Angew. Chem. Int. Ed. 2000, 39, 2768
74. J. V. Kingston, J. G. Verkade, J. Org. Chem. 2007, 72, 2816
75. J. P. Bezombes, F. Carré, C. Chuit, R. J. P. Corriu, A. Mehdi, C. Reyé, J. Organomet. Chem. 1997, 535, 81
76. L. C. Pop, N. Katir, A. Castel, L. Silaghi-Dumitrescu, F. Delpech, I. Silaghi-Dumitrescu, H. Gornitzka, D. MacLeod-Carey, N. Saffon, J. Organomet. Chem. 2009, 694, 1562
77. S. E. Pipko, L. V. Bezgubenko, D. S. Anatoliy, E. B. Rusanov, E. G. Kapustin, M. I. Povolotskii, V. V. Shvadchak, Heteroat. Chem. 2008, 19, 171
78. B. Fischer, L. Sheihet, J. Org. Chem. 1998, 63, 393; for a study on the C-phosphorylation of nitriles of carboxylic acids by phosphorus trichloride, see
79. D. M. Malenko, Y. G. Gololobov, Zh. Obshch. Khim. 1981, 51, 2629.
80. For a study on the quinuclidine versus the quinoline moiety for the N-C bond formation in cinchona alkaloids, see:, M. Baidya, M. Horn, H. Zipse, H. Mayr, J. Org. Chem. 2009, 74, 7157.
81. For examples of the dependence of the stereoselectivity on catalyst loading, see
82. H. Okamura, Y. Nakamura, T. Iwagawa, M. Nakatani, Chem. Lett. 1996, 25, 193
83. J. Lõpez-Cantarero, M. B. Cid, T. B. Poulsen, M. Bella, J. L. García Ruano, K. A. Jørgensen, J. Org. Chem. 2007, 72, 7062.
84. For examples of cinchona alkaloid allylic nucleophilic activation of electrophiles, see
85. H. L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, Y. C. Chen, Angew. Chem. 2009, 121, 5847
86. Angew. Chem. Int. Ed. 2009, 48, 5737
87. D. J. V. C. van-Steenis, T. Marcelli, M. Lutz, A. L. Spek, J. H. Maarseveen, H. Hiemstra, Adv. Synth. Catal. 2007, 349, 281; for an example of cinchona alkaloid nucleophilic activation of fluorine, see
88. T. Ishimaru, N. Shibata, T. Horikawa, N. Yasuda, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. 2008, 120, 4225
89. Angew. Chem. Int. Ed. 2008, 47, 4157.