One-Pot, Two-Step Protocol for the Catalytic Asymmetric Synthesis of Optically Active N,O- and O,O-Acetals

ChemCatChem

Volumn 5, Issue 6, 2013, Pages 1334-1339

  Polat, M Fatih ^a   Hettmanczyk, Lara ^a   Zhang, Wei ^a   Szabo, Zoltan ^a   Franzén, Johan ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Acetals; Asymmetric catalysis; Conjugate addition; Heterocycles; Organocatalysis

Indexed keywords

EID: 84878499424     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201200860     Document Type: Article

References (110)

1. A. Schmidt, D. Michalik, S. Rotzoll, E. Ullah, C. Fischer, H. Reinke, H. Görls c, P. Langer, Org. Biomol. Chem. 2008, 6, 2804.
2. V. Dumontet, N. VanHung, M.-T. Adeline, C. Riche, A. Chiaroni, T. Sévenet, F. Guéritte, J. Nat. Prod. 2004, 67, 858.
3. J. P. A. A. Brown, Mutat. Res. 1980, 75, 243;
4. M. Sano, M. Suzuki, T. Miyase, K. Yoshino, M. Maeda-Yamamoto, J. Agric. Food Chem. 1999, 47, 1906;
5. T. Ariga, M. Hamamoto, Fragrance J. 1994, 22, 52.
6. C. A. J. Erdelmeier, U. Regenass, T. Rali, O. Sticher, Planta Med. 1992, 58, 43.
7. M. Lamidi, M. Gasquet, E. Ollivier, L. N. Ekekang, G. Balansard, Pharm. Pharmacol. Lett. 1996, 6, 31.
8. Y. Y. Deeni, H. S. N. Hussain, J. Ethnopharmacol. 1991, 35, 91;
9. M. J. Chen, L. L. Hou, Zhiwu Xuebao 1984, 26, 280.
10. Z. Shen, Z. Chen, L. Li, W. Lei, X. Hao, Planta Med. 2000, 66, 287;
11. L. Li, Y.-M. Shen, X.-S. Yang, G.-Y. Zuo, Z.-J. Shen, Z.-H. Chen, X.-J. Hao, Eur. J. Pharmacol. 2002, 449, 23;
12. L. Li, J. Nie, Z. Shen, W. Wu, Z. Chen, X. Hao, Planta Med. 2001, 67, 142;
13. L. Li, Y.-M. Shen, X.-S. Yang, W.-L. Wu, B.-G. Wang, Z.-H. Chen, X.-J. Hao, Brain Res. 2002, 944, 205.
14. X.-J. Hao, J.-L. Nie, Phytochemistry 1998, 48, 1213.
15. A. Jossang, H. E. Bitar, V. C. Pham, T. Sévenet, J. Org. Chem. 2003, 68, 300;
16. J. Kobayashi, H. Takatsu, Y. C. Shen, H. Morita, Org. Lett. 2003, 5, 1733;
17. H. Morita, J. Kobayashi, Org. Lett. 2003, 5, 2895;
18. H. Morita, H. Takatsu, J. Kobayashi, Tetrahedron 2003, 59, 3575.
19. A. Ishii, K. Higashiyama, K. Mikami, Synlett 1997, 1381;
20. A. Ishii, F. Miyamoto, K. Higashiyama, K. Mikami, Tetrahedron Lett. 1998, 39, 1199;
21. A. Ishii, F. Miyamoto, K. Higashiyama, K. Mikami, Chem. Lett. 1998, 119;
22. J. Jiang, R. J. DeVita, G. A. Doss, M. T. Goulet, M. J. Wyvratt, J. Am. Chem. Soc. 1999, 121, 593;
23. N. A. Magnus, P. N. Confalone, L. Storace, Tetrahedron Lett. 2000, 41, 3015;
24. N. Lebouvier, C. Laroche, F. Huguenot, T. Brigaud, Tetrahedron Lett. 2002, 43, 2827;
25. F. Gosselin, A. Roy, P. D. O'Shea, C. Chen, R. P. Volante, Org. Lett. 2004, 6, 641;
26. C. K. Miao, R. Soreck, P.-J. Jones, Tetrahedron Lett. 1993, 34, 2259;
27. N. Yamazaki, T. Kusanagi, C. Kibayashi, Tetrahedron Lett. 2004, 45, 6509;
28. T. Itoh, N. Yamazaki, C. Kibayashi, Org. Lett. 2002, 4, 2469;
29. N. Yamazaki, W. Dokoshi, C. Kibayashi, Org. Lett. 2001, 3, 193-196;
30. N. Yamazaki, T. Itoh, C. Kibayashi, Tetrahedron Lett. 1999, 40, 739;
31. M. F. Mechelke, A. I. Meyers, Tetrahedron Lett. 2000, 41, 4339;
32. A. G. Waterson, A. I. Meyers, J. Org. Chem. 2000, 65, 7240.
33. H. Matsutani, S. Ichikawa, J. Yaruva, T. Kasumoto, T. Hiyama, J. Am. Chem. Soc. 1997, 119, 4541;
34. S. G. Davies, L. M. A. R. B. Correia, Chem. Commun. 1996, 1803;
35. M. D. Spantulescu, M. A. Boudreau, J. C. Vederas, Org. Lett. 2009, 11, 645;
36. M. Uchiyama, M. Oka, S. Harai, A. Ohta, Tetrahedron Lett. 2001, 42, 1931;
37. S. D. Rychnovsky, B. M. Bax, Tetrahedron Lett. 2000, 41, 3593.
38. S. J. Fletcher, C. M. Rayner, Tetrahedron Lett. 1999, 40, 7139;
39. G. S. Weatherhead, J. H. Houser, J. G. Ford, J. Y. Jamieson, R. R. Schrock, A. H. Hoveyda, Tetrahedron Lett. 2000, 41, 9553;
40. A. H. Hoveyda, R. R. Schrock, Chem. Eur. J. 2001, 7, 945;
41. S. D. Burke, N. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827;
42. H. Frauenrath, T. Philipps, Angew. Chem. 1986, 98, 261; Angew. Chem. Int. Ed. Engl. 1986, 25, 274;
43. H. Frauenrath, S. Reim, A. Wiesner, Tetrahedron: Asymmetry 1998, 9, 1103.
44. For asymmetric catalytic preparation of N, N-aminals, see
45. G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005, 127, 15696;
46. Y. Liang, E. B. Rowland, G. B. Rowland, J. A. Perman, J. C. Antilla, Chem. Commun. 2007, 4477.
47. H. Nagano, T. Katsuki, Chem. Lett. 2002, 31, 782. For an attempt at direct asymmetric carbonyl acetalization, see:
48. P. Barbaro, C. Bianchini, W. Oberhauser, A. Togni, J. Mol. Catal. A 1999, 145, 139.
49. F. Saitoh, H. Nishida, T. Mukaihira, K. Aikawa, K. Mikami, Eur. J. Org. Chem. 2006, 2269.
50. I. Čorić, S. Vellalath, B. List, J. Am. Chem. Soc. 2010, 132, 8536;
51. H. Nagano, T. Katsuki, Chem. Lett. 2002, 31, 782.
52. I. Čorić, B. List, Nature 2012, 438, 315.
53. G. Li, F. R. Fronczek, J. C. Antilla, J. Am. Chem. Soc. 2008, 130, 12216;
54. S. Vellalath, I. Coric, B. List, Angew. Chem. 2010, 122, 9943; Angew. Chem. Int. Ed. 2010, 49, 9749.
55. Z. Jin, X. Wang, H. Huang, X. Liang, J. Ye, Org. Lett. 2011, 13, 564.
56. W. Zhang, J. Bah, A. Wohlfarth, J. Franzén, Chem. Eur. J. 2011, 17, 13814;
57. W. Zhang, J. Franzén, Adv. Synth. Catal. 2010, 352, 499;
58. J. Franzén, A. Fisher, Angew. Chem. 2009, 121, 801; Angew. Chem. Int. Ed. 2009, 48, 787.
59. For organocatalytic conjugate addition of diketones, see:
60. S. P. Lathrop, T. Rovis, J. Am. Chem. Soc. 2009, 131, 13628;
61. P. T. Franke, R. L. Johansen, S. Bertelsen, K. A. Jørgensen, Chem. Asian J. 2008, 3, 216;
62. J. L. GarcíaRuano, V. Marcos, J. A. Suanzes, L. Marzo, J. Aleman, Chem. Eur. J. 2009, 15, 6576. For selected examples of organocatalytic conjugate addition of malonates and β-ketoesters see;
63. S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411; Angew. Chem. Int. Ed. 2006, 45, 4305;
64. A. Carlone, S. Cabrera, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 1119; Angew. Chem. Int. Ed. 2007, 46, 1101;
65. A. Carlone, M. Marigo, C. North, A. Landa, K. A. Jørgensen, Chem. Commun. 2006, 4928;
66. M. Rueping, A. Kuenkel, F. Tato, J. W. Bats, Angew. Chem. 2009, 121, 3754; Angew. Chem. Int. Ed. 2009, 48, 3699.
67. For general reviews on organocatalytic conjugate addition, see:
68. K. L. Jensen, G. Dickmeiss, H. Jiang, L. Albrecht, K. A. Jørgensen, Acc. Chem. Res. 2012, 45, 248;
69. L.-W. Xu, L. Li, Z.-H. Shi, Adv. Synth. Catal. 2010, 352, 243;
70. A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922;
71. C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042; Angew. Chem. Int. Ed. 2006, 45, 7876;
72. A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416;
73. J. L. Vicario, D. Bada, L. Carillo, Synthesis 2007, 2065;
74. D. Almaşi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 299;
75. S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701.
76. P. T. Franke, B. Richter, K. A. Jørgensen, Chem. Eur. J. 2008, 14, 6317;
77. Y. Lee, S. Woo, S.-G. Kim, Adv. Synth. Catal. 2011, 353, 2671;
78. M. Rueping, E. Sugiono, E. Merino, Angew. Chem. 2008, 120, 3089; Angew. Chem. Int. Ed. 2008, 47, 3046;
79. M. Rueping, E. Merino, E. Sugiono, Adv. Synth. Catal. 2008, 350, 2127;
80. M. Rueping, E. Sugiono, E. Merino, Chem. Eur. J. 2008, 14, 6329;
81. C. Yu, F. Zheng, H. Ye, W. Zhong, Tetrahedron 2009, 65, 10016;
82. M. Rueping, E. Merino, E. Sugiono, ChemCatChem 2012, 4, 987.
83. For recent general reviews on cascade/domino/one-pot reactions, see:
84. C. M. Marson, Chem. Soc. Rev. 2012, 41, 7712;
85. L.-F. Tietze, G. Brasche, K. M. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006;
86. K. C. Nicolaou, J. S. Chen, Chem. Soc. Rev. 2009, 38, 2993;
87. C. J. Chapman, C. G. Frost, Synthesis 2007, 1. For recent reviews on organocatalytic domino reactions, see:
88. A.-N. Alba, X. Companyo, M. Viciano, R. Rios, Curr. Org. Chem. 2009, 13, 1432;
89. X. Yu, W. Wang, Org. Biomol. Chem. 2008, 6, 2037;
90. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232; Angew. Chem. Int. Ed. 2008, 47, 6138;
91. D. Enders, C. Grondal, M. R. M. Höttl, Angew. Chem. 2007, 119, 1590; Angew. Chem. Int. Ed. 2007, 46, 1570.
92. For recent selected examples on organocatalytic one-pot reactions, see
93. H. Ishikawa, M. Honma, Y. Hayashi, Angew. Chem. 2011, 123, 2876; Angew. Chem. Int. Ed. 2011, 50, 2824;
94. H. Ishikawa, T. Suzuki, Y. Hayashi, Angew. Chem. 2009, 121, 1330; Angew. Chem. Int. Ed. 2009, 48, 1304;
95. S. Zhu, S. Yu, Y. Wang, D. Ma, Angew. Chem. 2010, 122, 4760; Angew. Chem. Int. Ed. 2010, 49, 4656;
96. A. Michrowska, B. List, Nat. Chem. 2009, 1, 225.
97. The absolute configuration was postulated to be analogous to the previously established absolute configuration of the conjugate addition adduct obtained through the reaction of acetyl acetone 3a and 2c catalyzed by pyrrolidine 4b; see Ref.[21a].
98. As was reported by Rovis etal. (see Ref.[21a]).
99. 1HNMR experiment.