Enantioselective activation of aldehydes by chiral phosphoric acid catalysts in an aza-ene-type reaction between glyoxylate and enecarbamate

Angewandte Chemie - International Edition

Volumn 47, Issue 22, 2008, Pages 4122-4125

  Terada, Masahiro ^a   Soga, Kazuyo ^a   Momiyama, Norie ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Asymmetric catalysis; Br nsted acids; Ene reactions; Phosphoric acids; Transition states

Indexed keywords

ACIDS; ALDEHYDES; CHEMICAL REACTIONS; COMPUTATIONAL METHODS; ENANTIOSELECTIVITY; HYDROGEN; HYDROGEN BONDS; ORGANIC COMPOUNDS; PHOSPHORIC ACID;

ASYMMETRIC CATALYSIS; ENE REACTIONS; PHOSPHORIC ACIDS; TRANSITION STATES;

CATALYSIS;

EID: 48249127121     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800232     Document Type: Article

References (83)

1. Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991.
2. For reviews on chiral Brønsted acid catalysis, see: a) P. M. Pihko, Angew. Chem. 2004, 116, 2110-2113;
3. Angew. Chem. Int. Ed. 2004, 43, 2062-2064;
4. b) M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573;
5. Angew. Chem. Int. Ed. 2006, 45, 1520-1543;
6. c) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999-1010;
7. d) S. J. Connon, Angew. Chem. 2006, 118, 4013-4016;
8. Angew. Chem. Int. Ed. 2006, 45, 3909-3912;
9. e) A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743;
10. f) T. Akiyama, Chem. Rev. 2007, 107, 5744-5758.
11. A. Berkessel, H. Gröger, Asymmetric Organocatalysis-From Biomimetic Concepts to Powerful Methods for Asymmetric Synthesis, Wiley-VCH, Weinheim, 2005.
12. a) Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146;
13. b) A. N. Thadani, A. R. Stankovic, V. H. Rawal, Proc. Natl. Acad. Sci. USA 2004, 101, 5846-5850;
14. c) A. K. Unni, N. Takenaka, H. Yamamoto, V. H. Rawal, J. Am. Chem. Soc. 2005, 127, 1336-1337;
15. d) V. B. Gondi, M. Gravel, V. H. Rawal, Org. Lett. 2005, 7, 5657-5660;
16. e) J. D. McGilvra, A. K. Unni, K. Modi, V. H. Rawal, Angew. Chem. 2006, 118, 6276-6279;
17. Angew. Chem. Int. Ed. 2006, 45, 6130-6133;
18. Also see: f) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289-296;
19. g) T. Schuster, M. Bauch, G. Dürner, M. W. Göbel, Org. Lett. 2000, 2, 179-181.
20. a) H. Du, D. Zhao, K. Ding, Chem. Eur. J. 2004, 10, 5964-5970;
21. b) W. Zhuang, T. B. Poulsen, K. A. Jørgensen, Org. Biomol. Chem. 2005, 3, 3284-3289;
22. c) T. Tonoi, K. Mikami, Tetrahedron Lett. 2005, 46, 6355-6358.
23. Intramolecular reaction, see: d) L. Zu, J. Wang, H. Li, H. Xie, W. Jiang, W. Wang, J. Am. Chem. Soc. 2007, 129, 1036-1037.
24. a) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357;
25. b) D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804-11805;
26. c) D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2005, 127, 9360-9361;
27. d) M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. 2006, 118, 2312-2315;
28. Angew. Chem. Int. Ed. 2006, 45, 2254-2257;
29. e) M. Terada, K. Sorimachi, D. Uraguchi, Synlett 2006, 133-136;
30. f) I. D. Gridnev, M. Kouchi, K. Sorimachi, M. Terada, Tetrahedron Lett. 2007, 48, 497-500;
31. g) M. Terada, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 292-293;
32. h) M. Terada, S. Yokoyama, K. Sorimachi, D. Uraguchi, Adv. Synth. Catal. 2007, 349, 1863-1867;
33. i) M. Terada, K. Machioka, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 10336-10337.
34. For selected examples of activation of imines: a) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594;
35. Angew. Chem. Int. Ed. 2004, 43, 1566-1568;
36. b) R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84-86;
37. c) J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc. 2006, 128, 1086-1087;
38. d) M. Rueping, E. Sugiono, C. Azap, Angew. Chem. 2006, 118, 2679-2681;
39. Angew. Chem. Int. Ed. 2006, 45, 2617-2619;
40. e) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765-3768;
41. Angew. Chem. Int. Ed. 2006, 45, 3683-3686;
42. f) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2006, 118, 4914-4916;
43. Angew. Chem. Int. Ed. 2006, 45, 4796-4798;
44. g) T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc. 2006, 128, 13070-13071;
45. h) X.-H. Chen, X.-Y. Xu, H. Liu, L.-F. Cun, L.-Z. Gong, J. Am. Chem. Soc. 2006, 128, 14802-14803;
46. i) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 6903-6907;
47. Angew. Chem. Int. Ed. 2006, 45, 6751-6755;
48. j) M. Rueping, C. Azap, Angew. Chem. 2006, 118, 7996-7999;
49. Angew. Chem. Int. Ed. 2006, 45, 7832-7835;
50. k) Q. Kang, Z.-A. Zhao, S.-L. You, J. Am. Chem. Soc. 2007, 129, 1484-1485;
51. l) G. Li, Y. Liang, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 5830-5831;
52. m) M. Yamanaka, J. Itoh, K. Fuchibe, T. Akiyama, J. Am. Chem. Soc. 2007, 129, 6756-6764;
53. n) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2007, 119, 4646-4649;
54. Angew. Chem. Int. Ed. 2007, 46, 4562-4565;
55. o) Q.-S. Guo, D.-M. Du, J. Xu, Angew. Chem. 2008, 120, 771-774;
56. Angew. Chem. Int. Ed. 2008, 47, 759-762.
57. Also see: p) E. B. Rowland, G. B. Rowland, E. Rivera-Otero, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 12084-12085.
58. D. Nakashima, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 9626-9627.
59. a) M. Rueping, W. Ieawsuwan, A. P. Antonchick, B. J. Nachtsheim, Angew. Chem. 2007, 119, 2143-2146;
60. Angew. Chem. Int. Ed. 2007, 46, 2097-2100;
61. b) M. Rueping, B. J. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem. 2008, 120, 603-606;
62. Angew. Chem. Int. Ed. 2008, 47, 593-596.
63. a) R. Matsubara, Y. Nakamura, S. Kobayashi, Angew. Chem. 2004, 116, 1711-1713;
64. Angew. Chem. Int. Ed. 2004, 43, 1679-1681;
65. b) R. Matsubara, Y. Nakamura, S. Kobayashi, Angew. Chem. 2004, 116, 3320-3322;
66. Angew. Chem. Int. Ed. 2004, 43, 3258-3260;
67. c) R. Matsubara, P. Vital, Y. Nakamura, H. Kiyohara, S. Kobayashi, Tetrahedron 2004, 60, 9769-9784;
68. d) J. S. Fossey, R. Matsubara, P. Vital, S. Kobayashi, Org. Biomol. Chem. 2005, 3, 2910-2913;
69. e) R. Matsubara, N. Kawai, S. Kobayashi, Angew. Chem. 2006, 118, 3898-3900;
70. Angew. Chem. Int. Ed. 2006, 45, 3814-3816;
71. f) H. Kiyohara, R. Matsubara, S. Kobayashi, Org. Lett. 2006, 8, 5333-5335;
72. g) R. Matsubara, S. Kobayashi, Angew. Chem. 2006, 118, 8161-8163;
73. Angew. Chem. Int. Ed. 2006, 45, 7993-7995;
74. h) R. Matsubara, T. Doko, R. Uetake, S. Kobayashi, Angew. Chem. 2007, 119, 3107-3110;
75. Angew. Chem. Int. Ed. 2007, 46, 3047-3050;
76. i) F. Berthiol, R. Matsubara, N. Kawai, S. Kobayashi, Angew. Chem. 2007, 119, 7949-7951;
77. Angew. Chem. Int. Ed. 2007, 46, 7803-7805.
78. For hydrogen bonding in complexes of Lewis acids with formyl hydrogen atoms, see: E. J. Corey, T. Lee, Chem. Commun. 2001, 1312-1329.
79. In the absence of 4 Å molecular sieves, the enantioselectivity was irreproducible (from 48 to 88%ee). This problem was circumvented by the addition of 4 Å molecular sieves, which scavenges adventitious acid that could contaminate the glyoxylate. For 4 Å molecular sieves as an acid scavenger, see: M. Terada, T. Ikehara, H. Ube, J. Am. Chem. Soc. 2007, 129, 14112-14113, and references therein.
80. P. Herold, A. F. Indolese, M. Studer, H. P. Jalett, U. Siegrist, H. U. Blaser, Tetrahedron 2000, 56, 6497-6499.
81. See the Supporting Information for the details of the DFT computational analysis.
82. For X-ray crystallographic analysis of a two-hydrogen-bonding interaction between carboxylic acid and dimethylformamide, see: a) M. Czugler, J. J. Stezowski, E. Weber, J. Chem. Soc. Chem. Commun. 1983, 154-155;
83. b) I. Csöregh, A. Sjögren, M. Czugler, M. Cserzö, E. Weber, J. Chem. Soc. Perkin Trans. 2 1986, 507-513.