Synthesis of solution-phase phosphoramidite and phosphite ligand libraries and their in situ screening in the rhodium-catalyzed asymmetric addition of arylboronic acids

Journal of Combinatorial Chemistry

Volumn 9, Issue 3, 2007, Pages 407-414

  Jagt, Richard B C ^a   Toullec, Patrick Y ^a   Schudde, Ebe P ^a   De Vries, Johannes G ^a,b   Feringa, Ben L ^a   Minnaard, Adriaan J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b Catalysis and Development   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; LIGAND; ORGANOPHOSPHORUS COMPOUND; PHOSPHITE; PHOSPHORAMIDOUS ACID; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; SOLUTION AND SOLUBILITY; STEREOISOMERISM; SYNTHESIS;

BORONIC ACIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; LIGANDS; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHITES; RHODIUM; SOLUTIONS; STEREOISOMERISM;

EID: 34249940684     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc060161k     Document Type: Article

References (89)

1. Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; Wiley: New York, 1994.
2. (a) De Vries, J. G.; De Vries, A. H. M. Eur. J. Org. Chem. 2003, 799.
3. (b) Gennari, C.; Piarulli, U. Chem. Rev. 2003, 103, 3071.
4. (c) Archibald, B.; Brummer, O.; Devenney, M.; Gorer, S.; Jandeleit, B.; Uno, T.; Weinberg W. H.; Weskamp. T. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Vol. 2, p 885.
5. (d) Hoveyda, A. H. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, Germany, 2002,;Vol. 2, p 991.
6. (a) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312.
7. (b) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773.
8. (c) Satyanarayana, T.; Kagan, H. B. Adv. Synth. Catal. 2005, 347, 737.
9. (a) Jandeleit, B.; Schaefer, D.; Powers, T. S.; Turner, H. W.; Weinberg, W. H. Angew. Chem., Int. Ed. 1999, 38, 2494.
10. (b) Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284.
11. (a) Reetz, M. T. Angew. Chem., Int. Ed. 2002, 41, 1335.
12. (b) Ref 2b.
13. (a) De Vries, J. G.; Lefort, L. Chem.-Eur. J. 2006, 12, 4722.
14. (b) Jäkel, C.; Paciello, R. Chem. Rev. 2006, 106, 2912.
15. Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217.
16. Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475.
17. Liu, G.; Ellmann, J. A. J. Org. Chem. 1995, 60, 7712.
18. (a) Cole, B. M.; Schimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 1996, 35, 1668.
19. (b) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 1997, 36, 1704.
20. (c) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
21. (d) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
22. (e) Brouwer, A. J.; Van der Linden, H. J.; Liskamp, R. M. J. J. Org. Chem. 2000, 65, 1750.
23. (f) Chataigner, I.; Gennari, C.; Piarulli, U.; Ceccarelli, S. Angew. Chem., Int. Ed. 2000, 39, 916.
24. In addition to the Gilbertson papers and the DSM/Groningen work, we are aware of only two other publications in this area, see: (a) Lapointe, A. M. J. Comb. Chem. 1999, 1, 101.
25. (b) Huttenloch, O.; Laxman, E.; Waldmann, H. Chem.-Eur. J. 2002, 8, 4767.
26. (a) Hoen, R.; Boogers, J. A. F.; Bernsmann, H.; Minnaard, A. J.; Meetsma, A.; Tiemersma-Wegman, T. D.; De Vries, A. H. M.; De Vries, J. G.; Feringa, B. L. Angew. Chem., Int. Ed. 2005, 44, 4209.
27. (b) Reetz, M. T.; Sell, T.; Meiswinkel, A.; Mehler, G. Angew. Chem., Int. Ed. 2005, 44, 790.
28. (a) Sandee, A. J.; Reek, J. N. H. Dalton Trans. 2006, 3385 and references therein.
29. (b) Breit, B. Angew. Chem., Int. Ed. 2005, 44, 6816.
30. (c) Takacs, J. M.; Chaiseeda, K.; Moteli, S. A.; Reddy, D. S.; Wu, D.; Chandra, K. Pure Appl. Chem. 2006, 78, 501.
31. (d) Kuil, M.; Goudriaan, P. E.; Van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Commun. 2006, 4679.
32. For the ring-opening of oxabicyclic alkenes, see: (a) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703. For desymmetrization of epoxides, see:
33. (b) Del Moro, F.; Crotti, P.; Di Bussolo, V.; Macchia, F.; Pineschi, M. Org. Lett. 2003, 5, 1971. For conjugate addition reactions, see:
34. (c) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
35. (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221.
36. (e) Lóez, F.; Minnaard, A. J.; Feringa, B. L. Acc. Chem. Res. 2007, 40, 179-188. For allylic alkylation reactions, see:
37. (f) Malda, H.; Van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169.
38. (g) Van Zijl, A. W.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Adv. Synth. Catal. 2004, 346, 413.
39. (h) Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 4435.
40. (i) Alexakis, A.; Malan, C.; Lea, L.; Tissot-Croset, K.; Polet, D.; Falciola, C. Chimia 2006, 124.
41. For allylic alkylation reactions, see: (a) Bartels, B.; Garcia-Yebra, C.; Helmchen, G. Eur. J. Org. Chem. 2003, 1097. For allylic amination reactions, see:
42. (b) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164.
43. (c) Lipowsky, G.; Helmchen, G. Chem. Commun. 2004, 116. For allylic etherification reactions, see:
44. (d) Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
45. (a) Howell, G. P.; Minnaard, A. J.; Feringa, B. L. Org. Biomol. Chem. 2006, 4, 1278. For an asymmetric intramolecular Heck reaction, see:
46. (b) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184.
47. c) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Chem. Soc., Dalton Trans. 2003, 2017.
48. For asymmetric hydrogenation reactions, see: (a) Van den Berg, M.; Feringa, B. L.; Minnaard, A. J. In Handbook of Homogeneous Hydrogenation; De Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 995.
49. (b) Panella, L.; Aleixandre, A. M.; Kruidhof, G. J.; Robertus, J.; Feringa, B. L.; De Vries, J. G.; Minnaard, A. J. J. Org. Chem. 2006, 71, 2026 and references cited therein. For asymmetric conjugate additions of aryl trifluoroborates, see:
50. (c) Duursma, A.; Boiteau, J.-G.; Lefort, L.; Boogers, J. A. F.; De Vries, A. H. M.; De Vries, J. G.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2004, 69, 8045.
51. (d) Duursma, A.; Lefort, L.; Boogers, J. A. F.; De Vries, A. H. M.; De Vries, J. G.; Minnaard, A. J.; Feringa, B. L. Org. Biomol. Chem. 2004, 2, 1682. For asymmetric conjugate additions of boronic acids, see:
52. (e) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 681;
53. Org. Lett. 2003, 5, 1385.
54. (f) Boiteau, J.-G.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2003, 68, 9481.
55. (g) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111.
56. (a) Lefort, A.; Boogers, J. A. F.; De Vries, A. H. M.; De Vries, J. G. Org. Lett 2004, 6, 1733.
57. (b) Duursma, A.; Lefort, L.; Boogers, J. A. F.; De Vries, A. H. M.; De Vries, J. G.; Minnaard, A. J.; Feringa, B. L. Org. Biomol. Chem. 2004, 2, 1682.
58. (c) Van den Berg, M.; Pena, D.; Minnaard, A. J.; Feringa, B. L.; Lefort, L.; Boogers, J. A. F.; De Vries, A. H. M.; De Vries, J. G. Chim. Oggi 2004, 22, 18.
59. Harms, A. F.; Hespe, W.; Nauta, W. T.; Rekker, R. F. Drug Design 1976, 6, 1.
60. For a recent review on catalytic asymmetric approaches toward enantiomerically enriched diarylmethanols and diarylmethylamines, see: Schmidt, F.; Stemmler, R. T.; Rudolph, J.; Bolm, C. Chem. Soc. Rev. 2006, 35, 454.
61. (a) For a recent review on metal-catalyzed asymmetric arylation reactions, see: Bolm, C.; Hildebrand, J. P.; Muñiz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284.
62. (b) For the asymmetric addition of aluminum reagents, see: Wu, K.-H.; Gau, H.-M. J. Am. Chem. Soc. 2006, 128, 14808.
63. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 2457.
64. (b) Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine; Hall, D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
65. Saikai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279.
66. (a) Jagt, R. B. C.; Toullec, P. Y.; De Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Biomol. Chem. 2006, 4, 773. Almost simultaneous with the publication of our results on this subject, a 1,1′-spirobiindane-7,7′-diol-based phosphite ligand was reported to provide enantioselectivites ranging from 62 to 87% ee, see:
67. (b) Duan, H.-F.; Xie, J.-H.; Shi, W.-J.; Zhang, Q.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2006, 8, 1479.
68. (a) Focken, T.; Rudolph, J.; Bolm, C. Synthesis 2005, 429.
69. (b) Moreau, C.; Hague, C.; Weller, A. S.; Frost, C. G. Tetrahedron Lett. 2001, 42, 6957.
70. (a) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976.
71. (b) Ueda, M.; Miyaura, N. J. Organomet. Chem. 2000, 595, 31.
72. Hayashi, T.; Kawai, M.; Tokunaga, N. Angew. Chem., Int. Ed. 2004, 43, 6125.
73. Kuriyama, M.; Soeta, T.; Hao, X.; Chen, Q.; Tomioka, K. J. Am. Chem. Soc. 2004, 126, 8128.
74. (a) Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 13584.
75. (b) Otomaru, Y.; Tokunaga, N.; Shintani, R.; Hayashi, T. Org. Lett. 2005, 7, 307.
76. For difficulties concerning the removal of the N-tosyl protecting group in this system, see ref 26 and Milburn, R. R.; Snieckus, V. Angew. Chem., Int. Ed. 2004, 43, 892 and references therein.
77. Weix, D. J.; Shi, Y.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 1092.
78. For the first example of this deprotection methodology, see ref 33.
79. Jagt, R. B. C.; Toullec, P. Y.; Geerdink, D.; De Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Angew. Chem., Int. Ed. 2006, 45, 2789.
80. Nozaki, K.; Sakai, T.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413.
81. Mixing experiments confirmed that the red color is caused by the combination of the remaining phosphorochloridite 2 and the rhodium precursor.
82. The highest enantioselectivity was obtained using 2-naphthyl carboxaldehyde as a substrate. The corresponding product was obtained in 92% isolated yield with 75% ee.
83. Conversions and enantioselectivities in different solvents were compared using the phosphoramidite Monophos as the chiral ligand.
84. Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095.
85. Bernsmann, H.; Van den Berg, M.; Hoen, R.; Minnaard, A. J.; Mehler, G.; Reetz, M. T.; De Vries, J. G.; Feringa, B. L. J. Org. Chem. 2005, 70, 943.
86. Peña, D.; Minnaard, A. J.; De Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552.
87. Arnold, L. A.; Imbos, R.; Mandoli, A.; De Vries, A. H. M.; Naasz, R.; Feringa, B. L. Tetrahedron 2000, 56, 2865.
88. Jagt, R. B. C.; De Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Lett. 2005, 7, 2433.
89. Toullec, P. Y.; Jagt, R. B. C.; De Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Lett. 2006, 8, 2715.