Catalytic asymmetric hydroperoxidation of α,β-unsaturated ketones: An approach to enantiopure peroxyhemiketals, epoxides, and aldols

Angewandte Chemie - International Edition

Volumn 47, Issue 42, 2008, Pages 8112-8115

  Reisinger, Corinna M ^a   Wang, Xingwang ^a   List, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Asymmetric catalysis; Epoxidation; Hydrogen peroxide; Ketones; Organocatalysis

Indexed keywords

AMINES; CATALYSIS; CHEMICAL REACTIONS; HYDROGEN; HYDROGEN PEROXIDE; KETONES; OXIDATION; REACTION KINETICS;

ASYMMETRIC CATALYSIS; CHEMICAL EQUATIONS; EFFICIENT; ENANTIOPURE; ENANTIOSELECTIVE; HYDROPEROXIDATION; ORGANOCATALYSIS; PRIMARY AMINES; UNSATURATED KETONES;

ORGANIC COMPOUNDS;

EID: 54049102496     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803238     Document Type: Article

References (81)

1. a) S. Juliá, J. Guixer, J. Masana, J. Rocas, S. Colonna, R. Annuziata, H. Molinari, J. Chem. Soc. Perkin Trans. 1 1982, 1317-1324;
2. b) H. Wynberg, B. Greijdanus, J. Chem. Soc. Chem. Commun. 1978, 427-428;
3. c) E. J. Corey, F.-Y. Zhang, Org. Lett. 1999, 1, 1287-1290;
4. d) O. Jacques, S. J. Richards, R. F. W. Jackson, Chem. Commun. 2001, 2712-2713;
5. e) T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974-5976;
6. f) W. Zhang, J. L. Loebach, S. R. Wilson, E. N. Jacobsen, J. Am. Chem. Soc. 1990, 112, 2801-2803;
7. g) R. Irie, K. Noda, Y. Ito, N. Matsumoto, T. Katsuki, Tetrahedron Lett. 1990, 31, 7345-7348;
8. h) D. Enders, J. Zhu, G. Raabe, Angew. Chem. 1996, 108, 1827-1829;
9. Angew. Chem. Int. Ed. Engl. 1996, 35, 1725-1728;
10. i) Z.-X. Wang, S. M. Miller, O. P. Anderson, Y. Shi, J. Org. Chem. 1999, 64, 6443-6458;
11. j) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329-2330;
12. k) S. Watanabe, T. Arai, H. Sasai, M. Bougauchi, M. Shibasaki, J. Org. Chem. 1998, 63, 8090-8091;
13. l) G. Peris, C. E. Jakobsche, S. J. Miller, J. Am. Chem. Soc. 2007, 129, 8710-8710;
14. m) A. Berkessel, M. Guixà, F. Schmidt, J. M. Neudröfl, J. Lex, Chem. Eur. J. 2007, 13, 4483-4498;
15. n) C. Li, E. A. Pace, M. C. Liang, E. Lobkovsky, T. D. Gilmore, J. A. Porco, Jr., J. Am. Chem. Soc. 2001, 123, 11308-11309;
16. o) W. Zhang, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 286-287;
17. p) A. Erkkilä, P. M. Pikho, M.-R. Clarke, Adv. Synth. Catal. 2007, 349, 802-806;
18. For reviews, see:q) W. Adam, C. R. Saha-Möller, P. A. Ganeshpure, Chem. Rev. 2001, 101, 3499-3548;
19. r) B. S. Lane, K. Burgess, Chem. Rev. 2003, 103, 2457-2474;
20. s) Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su, Chem. Rev. 2005, 105, 1603-1662;
21. t) M. J. Porter, J. Skidmore, Chem. Commun. 2000, 1215-1225;
22. u) A. Lattanzi, Curr. Org. Synth. 2008, 5, 117-133.
23. X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070-6071.
24. X. Lu, Y. Liu, B. Sun, B. Cindric, L. Deng, J. Am. Chem. Soc. 2008, 130, 8134-8135.
25. a) M. Marigo, J. Franzen, T. B. Poulsen, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 6964-6965;
26. b) S. Lee, D. W. C. MacMillan, Tetrahedron 2006, 62, 11413-11424;
27. c) X. Wang, B. List, Angew. Chem. 2008, 120, 1135-1138;
28. Angew. Chem. Int. Ed. 2008, 47, 1119-1122.
29. N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13368-13369.
30. For use in asymmetric enamine catalysis, see: a) S. H. McCooey, S. J. Connon, Org. Lett. 2007, 9, 599-602;
31. b) T.-Y. Liu, H.-L. Cui, Y. Zhang, K. Jiang, W. Du, Z.-Q. He, Y.-C. Chen, Org. Lett. 2007, 9, 3671-3674;
32. c) B.-L. Zheng, Q.-Z. Liu, C.-S. Guo, X.-L. Wang, L. He, Org. Biomol. Chem. 2007, 5, 2913-2915;
33. d) J. Zhou, V. Wakchaure, P. Kraft, B. List Angew. Chem. 2008, 120, 7768-7771;
34. Angew. Chem. Int. Ed. 2008, 47, 7656-7658;
35. for use in asymmetric iminium catalysis: e) G. Bartoli, P. Melchiorre, Synlett 2008, 1759-1772;
36. f) Y.-C. Chen, Synlett 2008, 1919-1930;
37. Vinylogous addition of α,α-dicyanoalkenes, see: g) J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393-396;
38. Angew. Chem. Int. Ed. 2007, 46, 389-392;
39. Addition of cyclic 1,3-dicarbonyl compounds, see: h) J.-W. Xie, L. Yue, W. Chen, W. Du, J. Zhu, J.-G. Deng, Y.-C. Chen, Org. Lett. 2007, 9, 413-415;
40. Indole alkylation, see: i) W. Chen, W. Du, L. Yue, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Org. Biomol. Chem. 2007, 5, 816-821;
41. j) G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403-1405;
42. 1,3-Dipolar cycloaddition, see: k) W. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen, Angew. Chem. 2007, 119, 7811-7814;
43. Angew. Chem. Int. Ed. 2007, 46, 7667-7670;
44. Oxa-Michael addition, see: l) A. Carlone, G. Bartoli, M. Bosco, F. Pesciaioli, P. Ricci, L. Sambri, P. Melchiorre, Eur. J. Org. Chem. 2007, 5492-5495;
45. Sulfa-Michael addition, see: m) P. Ricci, A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Adv. Synth. Catal. 2008, 350, 49-53;
46. Malononitrile addition, see: n) X. Li, L. Cun, C. Lian, L. Zhong, Y. Chen, J. Liao, J. Zhu, J. Deng, Org. Biomol. Chem. 2008, 6, 349-353;
47. Diels-Alder reaction, see: o) R. P. Singh, K. Bartelson, Y. Wang, H. Su, X. Lu, L. Deng, J. Am. Chem. Soc. 2008, 130, 2422-2423;
48. Epoxidation, see: p) Ref. [2];
49. tert-Alkyl peroxidation, see: q) Ref. [3];
50. For a review on primary amine catalysis, see: r) F. Peng, Z. Shao, J. Mol. Catal. A 2008, 285, 1-13.
51. a) Ref. [1d];
52. b) Ref [1h];
53. c) Ref. [1i];
54. d) Ref. [1j];
55. e) T. Ooi, D. Ohara, M. Tamura, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 6844-6845;
56. f) K. Daikai, T. Hayano, R. Kino, H. Furuno, T. Kagawa, J. Inanaga, Chirality 2003, 15, 83-88;
57. g) P. A. Bentley, S. Bergeron, M. W. Cappi, D. E. Hibbs, M. B. Hursthouse, T. C. Nugent, R. Pulido, S. M. Roberts, L. E. Wu, Chem. Commun. 1997, 739-740.
58. a) J. M. Fraile, J. I. García, J. A. Mayoral, S. Sebti, R. Tahir, Green Chem. 2001, 3, 271-274;
59. b) C. Cativiela, F. Figueras, J. M. Fraile, J. I. García, J. A. Mayoral, Tetrahedron Lett. 1995, 36, 4125-4128;
60. c) A. Rieche, E. Schmitz, E. Gründemann, Chem. Ber. 1960, 93, 2443-2448;
61. d) G. B. Payne, J. Org. Chem. 1958, 23, 310-311.
62. a) O. G. Kulinkovich, D. A. Astashko, V. I. Tyvorskii, N. A. Ilyina, Synthesis 2001, 1453-1455;
63. b) J.-P. Barnier, V. Morisson, L. Blanco, Synth. Commun. 2001, 31, 349-357.
64. a) D. A. Casteel, Nat. Prod. Rep. 1992, 9, 289-312;
65. b) A. J. Bloodworth, B. D. Bothwell, A. N. Collins, N. L. Maidwell, Tetrahedron Lett. 1996, 37, 1885-1888;
66. c) P. H. Dussault, X. Liu, Org. Lett. 1999, 1, 1391-1393;
67. d) P. Dai, T. K. Trullinger, X. Liu, P. H. Dussault, J. Org. Chem. 2006, 71, 2283-2292.
68. For the reduction of 3-hydroxy-1,2-dioxolanes with trivalent phosphorus compounds, see: a) A. L. Baumstark, P. C. Vasquez, Y. Chen, Heteroat. Chem. 1993, 4, 175-179;
69. b) V. Morisson, J.-P. Barnier, L. Blanco, Tetrahedron Lett. 1999, 40, 4045-4046.
70. For syntheses of β-hydroxy carbonyls by enantioselective catalytic conjugate additions, see: a) C. D. Vanderwal, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 14724-14725;
71. b) S. Bertelsen, P. Diner, R. L. Johansen, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 1536-1537;
72. c) Ref. [6k].
73. a) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575;
74. For a general review on enamine catalysis, see: b) S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569.
75. a) J. W. Yang, M. T. Hechavarria Fonseca, B. List, Angew. Chem. 2004, 116, 6829-6832;
76. Angew. Chem. Int. Ed. 2004, 43, 6660-6662;
77. b) J. W. Yang, M. T. Hechavarria Fonseca, N. Vignola, B. List, Angew. Chem. 2005, 117, 110-112;
78. Angew. Chem. Int. Ed. 2005, 44, 108-110;
79. c) S. Mayer, B. List, Angew. Chem. 2006, 118, 4299-4301;
80. Angew. Chem. Int. Ed. 2006, 45, 4193-4195;
81. For another study on the same reaction, see: d) S. G. Ouellet, J. B. Tuttle, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 32-33.