Monodentate Phosphoramidites: A Breakthrough in Rhodium-Catalysed Asymmetric Hydrogenation of Olefins

Advanced Synthesis and Catalysis

Volumn 345, Issue 1-2, 2003, Pages 308-323

  Van Den Berg, Michel ^a   Minnaard, Adriaan J ^a   Haak, Robert M ^a   Leeman, Michel ^a   Schudde, Ebe P ^a   Meetsma, Auke ^a   Feringa, Ben L ^a   De Vries, André H M ^b   Maljaars, C Elizabeth P ^b   Willans, Charlotte E ^b   Hyett, David ^b   Boogers, Jeroen A F ^b   Henderickx, Hubertus J W ^b   De Vries, Johannes G ^a,b  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b DSM Fine Chemicals Austria Nfg GmbH & Co KG   (Netherlands)

Author keywords

Asymmetric catalysis; Dehydroamino acids; Enamides; Hydrogenation; Monodentate phosphoramidite ligands; MonoPhos; P ligands; Rhodium

Indexed keywords

ALKENE; AMIDE; AMINO ACID DERIVATIVE; AROMATIC AMIDE; ESTER; HYDROGEN; ITACONIC ACID; LIGAND; METHYL 2 ACETAMIDOCINNAMATE; METHYL GROUP; O,O' (5,5',6,6',7,7',8,8' OCTAHYDRO 1,1' DINAPHTHYL 2,2' DIYL) N,N DIMETHYLPHOSPHORUS AMIDITE; RHODIUM; SOLVENT; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGENATION; MASS SPECTROMETRY; NONLINEAR SYSTEM; PRESSURE; SYNTHESIS; TURNOVER TIME;

EID: 0012327802     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200390026     Document Type: Article

References (127)

1. a) T. Ohkuma, M. Kitamura, R. Noyori, in Catalytic Asymmetric Synthesis, 2nd edn., (Ed.: I. Ojima), VCH Publishers Inc., New York, 2000, pp. 1-110;
2. b) S. A. Laneman, in Handbook of Chiral Chemicals, (Ed.: D. J. Ager), Marcel Dekker, Inc., New York, 1999, pp, 143-176;
3. c) J. M. Brown, in Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, Vol. 1, pp. 121-182;
4. d) A. Börner, J. Holz, in Transition Metals for Organic Synthesis. Building Blocks and Fine Chemicals, (Eds.: M. Beller, C. Bolm), Wiley-VCH, 1998, Vol. 2, pp. 3-13;
5. [1d], pp. 13-25;
6. f) M. Nógrádi, Stereoselective Synthesis, VCH, Weinheim, 1987, p. 53;
7. g) K. E. Koenig, in Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, Inc., Orlando, 1985, Vol, 5, p. 71.
8. R. Halterman, in Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, 1999, Vol. 1, p. 183.
9. a) W. S. Knowles, M. J. Sabacky, J. Chem. Soc. Chem. Commun. 1968, 1445;
10. b) W. S. Knowles, Acc. Chem. Res. 1983, 16, 106.
11. L. Horner, H. Siegel, H. Büthe, Angew. Chem. Int. Ed. Engl. 1968, 7, 942.
12. a) H. Brunner, W. Zettlmeier, Handbook of Enantioselectieve Catalysis, VCH, Weinheim, 1993;
13. b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1993;
14. c) H. B. Kagan, in Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, Inc., Orlando, 1985, Vol. 5, p. 1;
15. d) H. Brunner, Top. Stereochem. 1988, 18, 129.
16. H.-U. Blaser, F. Spindler, M. Studer, Appl. Catal. A: General 2001, 221, 119.
17. For reviews on the use of combinatorial methods in homogeneous catalysis, see: a) S. Dahmen, S. Bräse, Synthesis 2001, 1431; b) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. Int. Ed. 1999, 38, 2494; c) R. H. Crabtree, Chem. Commun. 1999, 1611; e) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885.
18. For reviews on the use of combinatorial methods in homogeneous catalysis, see: a) S. Dahmen, S. Bräse, Synthesis 2001, 1431; b) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. Int. Ed. 1999, 38, 2494; c) R. H. Crabtree, Chem. Commun. 1999, 1611; e) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885.
19. For reviews on the use of combinatorial methods in homogeneous catalysis, see: a) S. Dahmen, S. Bräse, Synthesis 2001, 1431; b) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. Int. Ed. 1999, 38, 2494; c) R. H. Crabtree, Chem. Commun. 1999, 1611; e) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885.
20. For reviews on the use of combinatorial methods in homogeneous catalysis, see: a) S. Dahmen, S. Bräse, Synthesis 2001, 1431; b) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. Int. Ed. 1999, 38, 2494; c) R. H. Crabtree, Chem. Commun. 1999, 1611; e) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885.
21. B. L. Feringa, Acc. Chem. Res. 2000, 33, 346 and references cited therein.
22. For the synthesis of a library of bispidine-based phosphoramidites, see: O. Huttenloch, E. Laxman, H. Waldmann, Chem. Commun. 2002, 673.
23. a) T. P Dang, H. B. Kagan, J. Chem. Soc. Chem. Commun. 1971, 481;
24. b) H. B. Kagan, T. P. Dang, J. Am. Chem. Soc. 1972, 94, 6429.
25. B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachman, D. J. Weinkauff, J. Am. Chem. Soc. 1977, 99, 5946.
26. W. S. Knowles, M. J. Sabacky, B. D. Vineyard, J. Chem. Soc. Chem. Commun. 1972, 10.
27. For a historical review on the use of chiral monodentate phosphine ligands in enantioselectieve olefin hydrogenations, see: I. V. Komarov, A. Börner, Angew. Chem. Int. Ed. 2001, 40, 1197.
28. a) R. Selke, H. Pracejus, J. Mol. Catal. 1986, 37, 213;
29. b) A. S. C. Chan, W. Hu, C.-C. Pai, C.-P. Lau, J. Am. Chem. Soc. 1997, 119, 9570;
30. c) Y. Chen, X. Li, S. K. Tong, M. C. K. Choi, A. S. C. Chan, Tetrahedron Lett. 1999, 40, 957;
31. d) T. V. RajanBabu, B. Radetich, K. K. You, T. A. Ayers, A. L. Casalnuovo, J. C. Calabrese, J. Org. Chem. 1999, 64, 3429;
32. e) K. Yonehara, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 9381.
33. a) M. T. Reetz, A. Gosberg, R. Goddard, S.-H. Kyung, Chem. Commun. 1998, 2077;
34. b) M. T. Reetz, T. Sell, Tetrahedron Lett. 2000, 41, 6333.
35. a) M. T. Reetz, T. Neugebauer, Angew. Chem. Int. Ed. 1999, 38, 179;
36. b) O. Pàmies, G. Net, A. Ruiz, C. Claver, Eur. J. Inorg. Chem. 2000, 1287.
37. A. Mortreux, F. Petit, G. Buono, G. Pfeiffer, Bull. Soc. Chim. France 1987, 631.
38. For a recent review, see: F. Lagasse, H. B. Kagan, Chem. Pharm. Bull. 2000, 48, 315.
39. a) M. van den Berg, A. J. Minnaard, E. P. Schudde, J. van Esch, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc. 2000, 122, 11539;
40. b) M. van den Berg, A. J. Minnaard, J. G. de Vries, B. L. Feringa, (DSM N.V), World Patent WO 02/04466, 2002.
41. a) C. Claver, E. Fernandez, A. Gillon, K. Heslop, D. J. Hyett, A. Martorell, A. G. Orpen, P. G. Pringle, Chem. Commun. 2000, 961;
42. b) M. T. Reetz, T. Sell, Tetrahedron Lett. 2000, 41, 6333.
43. M. T. Reetz, G. Mehler, Angew. Chem. Int. Ed. 2000, 39, 3889.
44. a) W. Chen, J. Xiao, Tetrahedron Lett. 2001, 42, 2897;
45. b) M. Ostermeier, J. Priess, G. Helmchen, Angew. Chem. Int. Ed., 2002, 41, 612;
46. c) Q. Zeng, H. Liu, X. Cui, A. Mi, Y. Jiang, X. Li, M. C. K. Choi, A. S. C. Chan, Tetrahedron: Asymmetry, 2002, 13, 115;
47. K. Junge, G. Oehme, A. Monsees, T. Riermeier, U. Dingerdissen, M. Beller, Tetrahedron Lett. 2002, 43, 4977.
48. a) Houben Weyl, Methoden der Organischen Chemie, (Ed.: E. Müller), Thieme, Stuttgart, 1964, Vol XII/2, p. 99;
49. b) R. S. Edmundson, in Comprehensive Organic Chemistry, (Eds., D. H. R. Barton, W. D. Ollis), Pergamon Press, Oxford, 1979, Vol. 2, part 10.3;
50. c) A. van Rooy, D. Burgers, P. C. J. Kamer, P. W. N. M. van -Leeuwen, Recl. Trav. Chim. Pays-Bas 1996, 115, 492.
51. A. H. M. de Vries, A. Meetsma, B. L. Feringa, Angew. Chem. Int. Ed. Engl. 1996, 35, 2374.
52. Y. H. Choi, J. Y. Choi, H. Y. Yang, Y. H. Kim, Tetrahedron: Asymmetry 2002, 13, 801.
53. R. Hulst, N. K. de Vries, B. L. Feringa, Tetrahedron: Asymmetry 1994, 5, 699.
54. a) S. L. Beaucage, R. P. Iyer, Tetrahedron 1992, 48, 2223;
55. b) A. Wilk, A. Grajkowski, L. R. Phillips, S. L. Beaucage, J. Am. Chem. Soc. 2000, 122, 2149.
56. 3N· HCl, pyridine·HCl, DMAP·HCl, imidazole, 3,4-dicyanoimidazole, benzimidazolium triflate and tetrazole. The latter two gave the best results.
57. Phosphoramidite amine-exchange has been reported in the synthesis of N-phosphorylamino acids, see: C. P. Chow, C. E. Berkman, Tetrahedron Lett. 1998, 39, 7471.
58. [8] and references cited therein;
59. b) F. Bertozzi, P. Crotti, F. Macchia, M. Pineschi, B. L. Feringa, Angew. Chem. Int. Ed. 2001, 40, 930;
60. c) R. Naasz, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Angew. Chem. Int. Ed. 2001, 40, 927.
61. d) F. Bertozzi, P. Crotti, B. L. Feringa, F. Macchia, M. Pineschi, Synthesis 2001, 483;
62. e) R. Imbos, A. J. Minnaard, B. L. Feringa, Tetrahedron 2001, 57, 2485;
63. f) R. Naasz, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Chem. Commun. 2001, 735,
64. g) L. A. Arnold, R. Naasz, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2001, 123, 5841;
65. h) A. Mandoli, L. A. Arnold, A. H. M. de Vries, P. Salvadori, B. L. Feringa, Tetrahedron: Asymmetry, 2001, 72, 1929;
66. i) F. Bertozzi, P. Crotti, F. Del Moro, B. L. Feringa, F. Macchia, M. Pineschi, Chem. Commun. 2001, 2606.
67. B. Bartels, G. Helmchen, Chem. Commun. 1999, 741.
68. H. Malda, A. W. van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169.
69. R. Imbos, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2002, 724, 184.
70. J. F. Jensen, B. Y. Svendsen, T. V. La Cour, H. L. Pedersen, M. Johannsen, J. Am. Chem. Soc. 2002, 124, 4558.
71. G. Franciò, F. Faraone, W. Leitner, J. Am. Chem. Soc. 2002, 124, 736.
72. Y. Fu, J.-H. Xie, A.-G. Hu, H. Zhou, L.-X. Wang, Q.-L. Zhou, Chem. Commun, 2002, 480.
73. A.-G. Hu, Y. Fu, J.-H. Xie, H. Zhou, L.-X. Wang, Q.-L. Zhou, Angew. Chem. Int. Ed. 2002, 41, 2348.
74. G. Franciò, F. Faraone, W. Leitner, Angew. Chem. Int. Ed. 2000, 39, 1428.
75. M. Diéguez, A. Ruiz, C. Claver, Chem. Commun. 2001, 2702.
76. a) H.-J. Drexler, W. Baumann, A. Spannenberg, C. Fischer, D. Heller, J. Organomet. Chem. 2001, 627, 89-102;
77. b) D. Heller, S. Borns, W. Baumann, R. Selke, Chem. Ber. 1996, 129, 85;
78. c) D. Heller, K. Kortus, R. Selke, Liebigs Ann. 1995, 575.
79. R. M. Herbst, D. Shemin, Organic Synthesis, Wiley, New York, 1943, Coll. Vol. II, p. 1.
80. a) A. S. Carlstroem, T. Frejd, Synthesis 1989, 414;
81. b) A. Arcadi, S. Cacchi, F. Marinelli, E. Morera, G. Ortar, Tetrahedron 1990, 46, 7151;
82. c) J. H. Dygos, E. E. Yonan, M. G. Scaros, O. J. Goodmonson, D. P. Getman, R. A. Periana, G. R. Beck, Synthesis 1992, 741.
83. We have developed an improved variant of the Heck reaction for the preparation of these substrates: C. Willans, A. H. M. de Vries, J. G. de Vries, manuscript in preparation.
84. D. A. Evans, J. L. Katz, G. S. Peterson, T. Hintermann, J. Am. Chem. Soc. 2001, 723, 12411.
85. Preparation of a library of ligands using parallel synthesis in an automatic synthesiser is currently underway.
86. D. J. Cram, R. C. Helgeson, S. C. Peacock, L. J. Kaplan, L. A. Domeier, P. Moreau, K. Koga, J. M. Mayer, Y. Chao, M. G. Siegel, D. H. Hoffmann, G. D. Y. Soga, J. Org. Chem. 1978, 43, 1930.
87. A similar profile would be obtained if the reaction was first order in substrate. We have at present no kinetic data to support this theory.
88. a) M. van den Berg, R. M. Haak, A. J. Minnaard, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Adv. Synth. Catal. 2002, 344, 1003;
89. b) Chan et al. have also published the use of 7a for the Rh-catalysed hydrogenation of enamides: X. Jia, R. Guo, X. Li, X. Yao, A. S. C. Chan, Tetrahedron Lett. 2002, 43, 5541.
90. M. J. Burk, G. Casy, N. B. Johnson, J. Org. Chem. 1998, 63, 6084.
91. Z. Zhang, G. Zhu, Q. Jiang, D. Xiao, X. Zhang, J. Org. Chem. 1999, 64, 1774.
92. See: M. J. Burk, Y. M. Wang, J. R. Lee, J. Am. Chem. Soc. 1996, 118, 5142 for a compilation of references.
93. The experiments of entries 2 and 3 were independently repeated 4 times to confirm this unexpected result. A referee has suggested that this effect may be due to the solvent (EtOAc) competing with one of the ester groups of the substrate for ligation at rhodium.
94. a) A. S. C. Chan, J. J. Pluth, J. Halpern, J. Am. Chem. Soc. 1980, 702, 5952;
95. b) J. M. Brown, P. A. Chaloner, J. Chem. Soc. Chem. Commun. 1980, 344.
96. I. D. Gridnev, N. Higashi, K. Asakura, T. Imamoto, J. Am. Chem. Soc. 2000, 122, 7183.
97. a) H. B. Kagan, T. O. Luukas, in Comprehensive Asymmetric Catalysis, (Eds.; E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, Vol. 1, p. 101;
98. b) for an early example from the Noyori labs, see: M. Kitamura, S. Okada, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028.
99. International Tables for Crystallography, 1983, Vol. A. Space-group symmetry, (Ed.: T. Hahn), Dordrecht, Reidel, (present distributor: Kluwer Academic Publishers, Dordrecht).
100. L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865.
101. For preparation of 3,3′-dimethyl-BINOL, see: D. S. Lingenfelter, R. C. Helgeson, D. J. Cram, J. Org. Chem. 1981, 46, 393.
102. E. Keller, J. Maurer, R. Naasz, T. Schader, A. Meetsma, B. L. Feringa, Tetrahedron: Asymmetry 1998, 9, 2409.
103. a) N. W. Boaz, S. D. Debenham, (Eastman Chemical Company), WO 02/026750, 2002;
104. b) W. Li, Z. Zhang, D. Xiao, X. Zhang, J. Org. Chem. 2000, 65, 3489;
105. c) J. J. A. Perea, M. Lotz, P. Knochel, Tetrahedron: Asymmetry, 1999,10, 375;
106. d) S. A. Laneman, D. E. Froen, D. J. Ager, in Catalysis of Organic Reactions, (Ed.: F. E. Herkes), Marcel Dekker, New York, 1998, p. 525;
107. e) T. V. RajanBabu, T. A. Ayers, G. A. Halliday, K. K. You, J. C. Calabrese, J. Org, Chem. 1997, 62, 6012;
108. f) M. J. Burk, Y. M. Wang, J. R. Lee, J. Am. Chem. Soc. 1996, 118, 5142;
109. g) A. Solladie-Cavallo, J. Schwarz, V. Burger, Tetrahedron: Asymmetry, 1994, 5, 1621;
110. h) M. J. Burk, J. E. Feaster, W. A. Nugent, R. L Harlow, J. Am. Chem. Soc. 1993, 115, 10125.
111. Bruker, 2000, SMART, SAINT, SADABS, XPREP and SHELXTL/NT. Area Detector Control and Integration Software. Smart Apex Software Reference Manuals. Bruker Analytical X-ray Instruments. Inc., Madison, Wisconsin, USA.
112. G. M. Sheldrick, 2001, SADABS. Version 2. Multi-Scan Absorption Correction Program. University of Göttingen, Germany.
113. A. J. M. Duisenberg, J. Appl. Cryst. 1992, 25, 92.
114. A. L. Spek, J. Appl. Cryst. 1988, 27, 578.
115. M. R. Snow, E. R. T. Tiekink, Acta Cryst. 1988, B44, 676.
116. Y. Le Page, J. Appl. Cryst. 1987, 20, 264.
117. Y. Le Page, J. Appl. Cryst. 1988, 27, 983.
118. P. T. Beurskens, G. Beurskens, R. de Gelder, S. García-Granda, R. O. Gould, R. Israël, J. M. M. Smits, 1999, The DIRDIF-99 program system, Crystallography Laboratory, University of Nijmegen, The Netherlands.
119. P. van der Sluis, A. L. Spek, Acta Cryst. 1990, A46, 194.
120. H. D. Flack, Acta. Cryst. 1983, A39, 876.
121. H. D. Flack, G. Bernardinelli, Acta Cryst. 1999, A55, 908.
122. H. D. Flack, G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143.
123. R. Herbst-Irmer, G. M. Sheldrick, Acta Cryst. 1998, B54, 443.
124. International Tables for Crystallography, 1992, Vol. C, (Ed.; A. J. C. Wilson), Kluwer Academic Publishers, Dordrecht, The Netherlands.
125. G. M. Sheldrick, 1997, SHELXL-97. Program for the Refinement of Crystal Structures. University of Göttingen, Germany.
126. A. Meetsma, 2002, PLUTO. Molecular Graphics Program. University of Groningen, The Netherlands.
127. A. L. Spek, 2002, PLATON. Program for the Automated Analysis of Molecular Geometry (A Multipurpose Crystallographic Tool), Version of February 2002, University of Utrecht, The Netherlands.