Preparation and Use of C2-Symmetric Bis(phospholanes): Production of α-Amino Acid Derivatives via Highly Enantioselective Hydrogenation Reactions

Journal of the American Chemical Society

Volumn 115, Issue 22, 1993, Pages 10125-10138

  Burk, Mark J ^a   Feaster, John E ^a   Nugent, William A ^a   Harlow, Richard L ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000740766     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00075a031     Document Type: Article

References (89)

1. Bosnich, B., Ed. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, 1986.
2. Kagan, H. B. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 1.
3. Koenig, K. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 3.
4. Ojima, I.; Clos, N.; Bastos, C. Tetrahedron 1989, 45, 6901.
5. Knowles, W. S. Acc. Chem. Res. 1983, 16, 106.
6. Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262.
7. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
8. Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 10, 2653.
9. Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569.
10. Burk, M. J.; Harlow, R. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 1462.
11. Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518.
12. Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266.
13. Burk, M. J.; Feaster, J. E. Tetrahedron Lett. 1992, 33, 2099.
14. Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
15. Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
16. Issleib, K.; Thorausch, P. Phosphorus Sulfur Relat. Elem. 1977, 3, 203.
17. Hey, E. J. Organomet. Chem. 1989, 378, 375.
18. Otsuka, S.; Nakamura, A.; Kano, G.; Tani, K. J. Am. Chem. Soc. 1971, 93, 4301.
19. Tani, K.; Brown, L. D.; Ahmed, T.; Ibers, J. A.; Yokota, M.; Nakamura, A.; Otsuka, S. J. Am. Chem. Soc. 1977, 99, 7876.
20. Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989.
21. Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B., Ed.; Marcel Dekker: New York, 1983; Vol. 7, pp 267–357.
22. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids; John Wiley and Sons: New York, 1987.
23. Roberts, D. C.; Vellaccio, F. In The Peptides; Gross, E., Meienhofer, J., Eds.; Academic Press: New York, 1983; Chapter 6.
24. Ball, R. G.; Payne, N. C. Inorg. Chem. 1977, 16, 1187.
25. McGinnety, J. A.; Payne, N. C.; Ibers, J. A. J. Am. Chem. Soc. 1969, 91, 6301.
26. Toriumi, K.; Ito, T.; Takaya, H.; Souchi, T.; Noyori, R. Acta Crystallogr. 1982, B32, 807.
27. Ball, R. G.; Payne, N. C. Inorg. Chem. 1977, 16, 1187.
28. Kyba, E. P.; Davis, R. E.; Juri, P. N.; Shirley, K. R. Inorg. Chem. 1981, 20, 3616.
29. Chaloner, P. A. Handbook of Coordination Catalysis in Organic Chemistry; Butterworth and Co.: London, 1986.
30. Parshall, G. W. Homogeneous Catalysis; Wiley-Interscience: New York, 1980.
31. Alyea, D. C., Meek, D. W., Eds. Catalytic Aspects of Metal Phosphine Complexes; Advances in Chem. Ser.; American Chemical Society: Washington, DC, 1982.
32. McAuliffe, C. A.; Levason, W. J. Phosphine, Arsine, and Stibine Complexes of the Transition Elements; Elsevier Scientific Publishing Col: Amsterdam, 1979.
33. Warren, L. F.; Bennett, M. A. Inorg. Chem. 1976, 15, 3126.
34. Liu, S.-T.; Chen, J.-T.; Peng, S.-M.; Hsiao, Y.-L.; Cheng, M.-C. Inorg. Chem. 1990, 29, 1169 and references there in.
35. Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1971, 93, 2397.
36. Appelt, A.; Ariaratnam, V.; Willis, A. C.; Wild, S. B. Tetrahedron; Asymmetry 1990, 1, 9.
37. Miedaner, A.; Haltiwanger, R. C.; DuBois, D. L. Inorg. Chem. 1991, 30, 417.
38. Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G. Chem. Ber. 1986, 119, 3326.
39. Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245.
40. Selke, R.; Pracejus, H. J. Mol. Cat. 1986, 37, 213.
41. Riley, D. P.; Shumate, R. E. J. Org. Chem. 1980, 45, 5187.
42. Takahashi, H.; Achiwa, K. Chem. Lett. 1989, 305.
43. Inoguchi, K.; Achiwa, K. Chem. Pharm. Bull. 1990, 38, 818.
44. Halpern, J. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press; New York, 1985; Vol. 5, Chapter 2.
45. Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746.
46. Ojima, I.; Kogure, T.; Yoda, N. J. Org. Chem. 1980, 45, 4728.
47. Nagel, U.; Rieger, B. Organometallics 1989, 8, 1534.
48. Brown, J. M.; Chaloner, P. A. J. Chem. Soc., Chem. Commun. 1980, 344.
49. Brown, J. M.; Murrer, B. A. J. Chem. Soc., Perkin Trans. II 1982, 489.
50. Chan, A. S. C.; Pluth, J. J.; Halpern, J. J. Am. Chem. Soc. 1980, 102, 5952.
51. Krause, H.-W.; Kreuzfeld, H. J.; Dobler, C.; Taudien, S. Tetrahedron: Asymmetry 1992, 3, 555.
52. Taudien, S.; Schinkowski, K.; Krause, H.-W. Tetrahedron: Asymmetry 1993, 4, 73.
53. Kovacs, J. In The Peptides: Analysis, Synthesis, and Biology; Gross, E.; Meienhofer, J., Eds.; Academic Press, New York, 1980; Vol. 2, pp 486.
54. Schmidt, U.; Weller, D.; Holder, A.; Lieberknecht, A. Tetrahedron Lett. 1988, 29, 3227.
55. Melillo, D.; Larsen, R. D.; Mathre, D. J.; Shukis, W. F.; Wood, A. W.; Colleluori, J. R. J.Org.Chem. 1987, 52, 5143.
56. Schmidt, U.; Liebernecht, A.; Kazmaier, U.; Griesser, H.; Jung, G.; Metzger, J. Synthesis 1991, 49.
57. Schmidt, U.; Meyer, R.; Leitenberger, V.; Stabler, F.; Lieberknecht, A. Synthesis 1991, 409.
58. Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487.
59. Berti, F.; Ebert, C.; Gardossi, L. Tetrahedron Lett. 1992, 33, 8145.
60. Bigge, C. F.; Wu, J.-P.; Drummond, J. T. Bioorg. Med. Chem. Lett. 1992, 2, 207.
61. Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159.
62. Scott, J. W.; Kieth, D. D.; Nix, G., Jr.; Parrish, D. R.; Remington, S.; Roth, G. P.; Townsend, J. M.; Valentine, D., Jr.; Yang, R. J. Org. Chem. 1981, 46, 5086.
63. Vineyard, B. D.; Knowles, W. S.;Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946.
64. Thompson, H. W.; McPherson, E. J. Am. Chem. Soc. 1974, 96, 6232.
65. Hussey, A. S.; Takeuchi, Y. J. Org. Chem. 1970, 35, 643.
66. Kirby, G. W.; Michael, J. J. Chem. Soc., Chem. Commun. 1971, 415.
67. Kirby, G. W.; Michael, J. J. Chem. Soc., Perkin Trans. 1 1973, 115.
68. Detellier, C.; Gelbard, G.; Kagan, H. B. J. Am. Chem. Soc. 1978, 100, 7556.
69. Koenig, K. E.; Knowles, W. S. J. Am. Chem. Soc. 1978, 100, 7561.
70. Landis, C. R.; Halpern, J. J. Organomet. Chem. 1983, 250, 485 and references therein.
71. March, J. Advanced Organic Chemistry 4th ed.; John Wiley and Sons, Inc.: New York, 1992; pp 109–111 and references therein.
72. König, Vf. A. The Practice of Enantiomer Separation by Capillary Gas Chromatography; Huthig Press: Heidelberg, 1987.
73. Schurig, V.; Nowotny, H.-P. Angew Chem., Int. Ed. Engl. 1990, 29, 939 and references therein.
74. Armstrong, S. K.; Brown, J. M.; Burk, M. J. Tetrahedron Lett. 1993, 879.
75. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, 1987; Chapter 10.
76. Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571.
77. King, S. A.; Thompson, A. S.; King, A. O.; Verhoeven, T. H. J. Org. Chem. 1992, 57, 6689.
78. Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856.
79. Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
80. Kitamura, M.; Sayo, N.; Noyori, R.; Shim, J.; Overman, L. E. Org. Synth. 1992, 71, 1.
81. Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Winkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946.
82. Wolf, J. P., III; Neimann, C. Biochemistry 1963, 2, 493.
83. Smart, N. A.; Young, G. T.; Williams, M. W. J. Chem. Soc. 1960, 3902.
84. Sinou, D.; Kagan, H. B. J. Organomet. Chem. 1976, 114, 325.
85. Jones, J. B.; Kunitake, T.; Niemann, C.; Hein, G. E. J. Am. Chem. Soc. 1965, 87, 1777.
86. Pattabiraman, T. N.; Lawson, W. B. Biochem. J. 1972, 126, 659.
87. Hayashi, Y.; Lawson, W. B. J. Biol. Chem. 1969, 244, 4158.
88. Cativiela, C.; Diaz de Villegas, M. D.; Garcia, J. I.; Mayoral, J. A.; Melendez, E. Bull. Soc. Chim. Belg. 1984, 93, 479.
89. Cativiela, C.; Fernandez, J.; Mayoral, J. A.; Melendez, E.; Uson, R.; Oro, L. A.; Fernandez, M. J. J. Mol. Cat. 1982, 16, 19.