Synthesis of versatile building blocks through asymmetric hydrogenation of functionalized itaconic acid mono-esters

Advanced Synthesis and Catalysis

Volumn 350, Issue 1, 2008, Pages 85-94

  Hekking, Koen F W ^a   Lefort, Laurent ^b   De Vries, André H M ^b   Van Delft, Floris L ^a   Schoemaker, Hans E ^b   De Vries, Johannes G ^b   Rutjes, Floris P J T ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b Catalysis and Development   (Netherlands)

Author keywords

Asymmetric catalysis; Asymmetric hydrogenation; Itaconic acid; Monodentate phosphoramidite ligands; Rhodium; Succinic acid

Indexed keywords

EID: 38349125966     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700307     Document Type: Article

References (81)

1. For recent reviews, see: a) The Handbook of Homogeneous Hydrogenation, (Eds. J. G. de Vries, C. J. Elsevier), Wiley-VCH, Weinheim, 2007, Vols. 1-3;
2. b) W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029;
3. c) W. S. Knowles, Angew. Chem. 2002, 114, 2096;
4. Angew. Chem. Int. Ed. 2002, 41, 1998;
5. d) T. Ohkuma, M. Kitamura, R. Noyori, in: Catalytic Asymmetric Synthesis, (Ed.: I. Ojima), Wiley-VCH, Weinheim, 2000, p 1;
6. e) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
7. An example of the application of such optically active building blocks in the synthesis of biologically relevant nitrogen heterocycles can be found in the subsequent paper in the current issue: K. F. W. Hekking, D. C. J Waalboer, M. A. H. Moelands, F. L. van Delft, F. P. J. T. Rutjes, Adv. Synth. Catal. following article in this issue.
8. M. Ostermeier, B. Brunner, C. Korff, G. Helmchen, Eur. J. Org. Chem. 2003, 3453, and references cited therein.
9. For recent examples, see: a) J. Almena, A. Monsees, R. Kadyrov, T. H. Riermeier, B. Gotov, J. Holz, A. Borner, Adv. Synth. Catal. 2004, 346, 1263;
10. b) S. Wu, M. He, X. Zhang, Tetrahedron: Asymmetry 2004, 15, 2177;
11. c) W Tang, D. Liu, X. Zhang, Org. Lett. 2003, 5, 205;
12. d) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118.
13. D. Carmichael, H. Doucet, J. M. Brown, Chem. Commun. 1999, 261.
14. a) M. J. Burk, F. Bienewald, M. Harris, A. Zanotti-Gerosa, Angew. Chem. 1998, 110, 2034;
15. Angew. Chem. Int. Ed. 1998, 37, 1931;
16. b) Y. Ito, T. Kamijo, H. Harada, F. Matsuda, S. Terashima, Tetrahedron Lett. 1990, 31, 2731;
17. c) T. Morimoto, M. Chiba, K. Achiwa, Tetrahedron Lett. 1989, 30, 735.
18. For reviews on asymmetric hydrogenation with monodentate phosphorus ligands, see: a) M. van den Berg, B. L. Feringa, A. J. Minnaard, in: The Handbook of Homogeneous Hydrogenation, Vol. 2, (Eds.: J. G. de Vries, C. J. Elsevier), Wiley-VCH, Weinheim, 2007, p 995;
19. nd edn., (Ed:. D. J. Ager), CRC (Taylor & Francis), Boca Raton, 2006, p 269;
20. c) T. Jerphagnon, J.-L. Renaud, C. Bruneau, Tetrahedron: Asymmetry 2004, 15, 2101.
21. For a recent review on the use of this ligand library in asymmetric hydrogenation, see: J. G. de Vries, L. Lefort, Chem. Eur. J. 2006, 12, 4722.
22. a) L. Panella, A. M. Aleixandre, G. J. Kruidhof, J. Robertus, B. L. Feringa, J. G. de Vries, A. J. Minnaard, J. Org. Chem. 2006, 71. 2026;
23. b) B. Bernsmann, M. van den Berg, R. Hoen, A. J. Minnaard, G. Mehler, M. T. Reetz, J. G. de Vries, B. L. Feringa, J. Org. Chem. 2005, 70, 943;
24. c) M. van den Berg, A. J. Minnaard, R. M. Haak, M. Leeman, E. P. Schudde, A. Meetsma, B. L. Feringa, A. H. M. de Vries, C. E. P. Maljaars, C. E. Willans, D. Heytt, J. A. F. Boogers, H. J. W. Henderickx, J. G. de Vries, Adv. Synth. Catal. 2003, 345, 308;
25. d) D. Peña, A. J. Minnaard, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc. 2002, 124, 14552;
26. e) 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.
27. L. Panella, B. L. Feringa, J. G. de Vries, A. J. Minnaard, Org. Lett. 2005, 7, 4177.
28. 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.
29. R. Hoen, J. A. F. Boogers, H. Bernsmann, A. J. Minnaard, A. Meetsma, T. D. Tiemersma-Wegman, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Angew. Chem. 2005, 117, 4281;
30. Angew. Chem. Int. Ed. 2005, 44, 4209.
31. J. W. Faller, S. C. Milheiro, J. Parr, J. Organomet. Chem. 2006, 691, 4945.
32. a) B. L. Feringa, Acc. Chem. Res. 2000, 33, 346;
33. b) B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos, A. H. M. de Vries, Angew. Chem. 1997, 109, 2733;
34. Angew. Chem. Int. Ed. 1997, 36, 2620.
35. J. F. Jensen, B. Y. Svendsen, T. V. La Cour, H. L. Pedersen, M. Johannsen, J. Am. Chem. Soc. 2002, 124, 4558.
36. a) G. Franciò, F. Faraone, W. Leitner, J. Am. Chem. Soc. 2002, 124, 736;
37. b) A. Zhang, T. V. RajanBabu, J. Am. Chem. Soc. 2006, 128, 54.
38. D. Huber, P. G. Anil Kumar, P. S. Pregosin, I. S. Mikhel, A. Mezetti, Helv. Chim. Acta 2006, 89, 1696.
39. a) B. Bartels, G. Helmchen, Chem. Commun. 1999, 741;
40. b) M. Schelwies, P. Dübon, G. Helmchen, Angew. Chem. 2006, 118, 2526;
41. Angew. Chem. Int. Ed. 2006, 45, 2466;
42. c) A. Leitner, S. Shekhar, M. J. Pouy, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 15506;
43. d) D. Polet, A. Alexakis, K. Tissot-Croset, C. Corminboeuf, K. Dietrich, Chem. Eur. J. 2006, 12, 3596;
44. e) I. Lyothier, C. Defieber, E. M. Carreira, Angew. Chem. 2006, 118, 6350;
45. Angew. Chem. Int. Ed. 2006, 45, 6204;
46. f) A. W. van Zijl, F. Lopez, A. J. Minnaard, B. L. Feringa, J. Org. Chem. 2007, 72, 2558.
47. B.-M. Fan, J.-H. Xie, S. Li, Y.-Q Tu, Q.-L. Zhou, Adv. Synth. Catal. 2005, 347, 759.
48. a) R. Imbos, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2002, 124, 184;
49. b) R. K. Thalji, J. A. Ellman, R. G. Bergman, J. Am. Chem. Soc. 2004, 126, 7192.
50. C. Böing, G. Franciò, W. Leitner, Chem. Commun. 2005 1456.
51. F. Boeda, P. Mosset, C. Crévisy, Tetrahedron Lett. 2006, 47, 5021.
52. R. T. Yu, T. Rovis, J. Am. Chem. Soc. 2006, 128, 12370.
53. a) R. B. C. Jagt, P. Y. Toldlec, D. Geerdink, J. G. de Vries, B. L. Feringa, A. D. J. Minnaard, Angew. Chem. 2006, 118, 2855;
54. Angew. Chem. Int. Ed. 2006, 45, 2789;
55. b) R. B. C. Jagt, P. Y. Toullec, J. G. de Vries, B. L. Feringa, A. J. Minnaard, Org. Biomol. Chem. 2006, 4, 613;
56. c) R. B. C. Jagt, P. Y. Toullec, E. P. Schudde, J. G. de Vries, B. L. Feringa, A. J. Minnaard, J. Comb. Chem. 2007, 9, 407;
57. d) C. Monti C, C. Gennari, U. Piarulli, Chem. Eur. J. 2007, 13, 1547.
58. a) R. Ballini, G. Bosica, A. Palmieri, M. Petrini, C. Pierantozzi, Tetrahedron 2003, 59, 7283;
59. b) R. Ballini, G. Bosica, D. Fiorini, P. Righi, Synthesis 2002, 681.
60. a) W. S. Johnson, G. H. Daub, Org. React. 1951, 6, 1;
61. b) H. Stobbe, Ber. dtsch. chem. Ges. 1893, 26, 2312.
62. L. Lefort, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, Org. Lett. 2005, 6, 1733.
63. http://www.biotage.com/DynPage.aspx?id = 23682.
64. The high conversion of 6c (91 %) compared to that of 6d (60%) can be ascribed to the gradual increase in pressure due to leakage from the hydrogen system into the reaction vessel of 6c.
65. Because of the structural similarity between 6c and 6d, we did not expect any significant differences in hydrogenation results. Therefore we decided to carry out the high-throughput experiment with one of these substrates (6d).
66. http://www.premex-reactorag.ch/e/spezialloesungen/produkteneuheiten/.
67. D, Peña, A.J. Minnaard, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Org. Lett. 2003, 5, 475.
68. a) M. T. Reetz, A. Meiswinkel, G. Mehler, K. Angermund, M. Graf, W. Thiel, R. Mynott, D. G. Blackmond, J. Am. Chem. Soc. 2005, 127, 10305;
69. b) M. T. Reetz, X. Li, Synthesis 2005, 3183;
70. c) M. T. Reetz, L. J. Goossen, A. Meiswinkel, J. Paetzold, J. Feldthusen Jensen, Org. Lett. 2003, 5, 3099;
71. d) M. T. Reetz, G. Mehler, Angew. Chem. 2000, 112, 4047;
72. Angew. Chem. Int. Ed. 2000, 39, 3889.
73. The poor results with L1 (entry A1), compared those observed in the Endeavor experiments, are remarkable and can probably be ascribed to unsuccessful ligand synthesis.
74. For a previous synthesis of L4, see: L. Lefort, J. A. F. Boogers, A. H. M. de Vries J. G. de Vries, Org. Lett. 2004, 6, 1733.
75. For a previous synthesis of L5, see: M. T. Reetz, L. J. Goossen. A. Meiswinkel, J. Paetzold, J. F. Jensen, Org. Lett. 2003, 5, 3099.
76. L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865.
77. R. N. Ram, I. Charles, Tetrahedron 1997, 53, 7335.
78. G. Sabitha, R. Srividya, J. S. Yadav, Tetrahedron 1999, 55, 4015.
79. K. Freudenberg, W. Lwowski, W. Hohmann, Liebigs Ann. Chem. 1955, 594, 76.
80. S. Mobashery, S. S. Ghosh, S. Y. Tamura, E. T. Kaiser, Proc. Natl. Acad. Sci. U. S. A. 1990, 87, 578.
81. Y. Caro, C. F. Masaguer, E. Ravina, Tetrahedron: Asymmetry 2003, 14, 381.