Asymmetric organocatalysis mediated by α,α-L-diaryl prolinols: Recent advances

Chemical Communications

Volumn 49, Issue 37, 2013, Pages 3821-3832

  Meninno, Sara ^a   Lattanzi, Alessandra ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE; AMINOALCOHOL; BRONSTED ACID; BRONSTED BASE; ENAMINE; EPOXIDE; ESTER; INDOLE DERIVATIVE; KETONE DERIVATIVE; PROLINOL DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; BAEYER VILLIGER REACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; CONJUGATION; COVALENT BOND; CRYSTALLIZATION; CYCLOADDITION; CYCLOPROPANATION; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; ENANTIOSELECTIVITY; EPOXIDATION; MICHAEL ADDITION; RING CLOSING METATHESIS; SUBSTITUTION REACTION; SULFENYLATION;

EID: 84879543822     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc36928e     Document Type: Article

References (107)

1. Enantioselective Organocatalysis: Reactions and Experimental Procedures, ed. P. I. Dalko, Wiley-VCH, Weinheim, 2007
2. Asymmetric Organocatalysis, ed. B. List, Springer, Berlin, 2010
3. C. Grondal, M. Jeanty, D. Enders: Nat. Chem. 2010 2:167.
4. E. Marqués-López, R. P. Herrera, M. Christmann: Nat. Prod. Rep. 2010 27:1138.
5. C. A. Busacca, D. R. Fandrick, J. J. Song, C. H. Senanayake: Adv. Synth. Catal. 2011 353:1825.
6. G. P. Howell: Org. Process Res. Dev. 2012 16:1258.
7. Hydrogen Bonding in Organic Synthesis, ed. P. M. Pihko, Wiley-VCH, Weinheim, 2009
8. Asymmetric Phase Transfer Catalysis, ed. K. Maruoka, Wiley-VCH, Weinheim, 2008
9. T. Akiyama: Chem. Rev. 2007 107:5744.
10. M. Terada: Synthesis 2010:1929.
11. T. Marcelli, J. H. van Maarseveen, H. Hiemstra: Angew. Chem., Int. Ed. 2006 45:7496.
12. A. G. Doyle, E. N. Jacobsen: Chem. Rev. 2007 107:5713.
13. S. J. Connon: Chem. Commun. 2008:2499.
14. C. Palomo, M. Oiarbide, R. López: Chem. Soc. Rev. 2009 38:632.
15. S. E. Denmark: Chimia 2008 62:37.
16. D. H. Paull, C. J. Abraham, M. T. Scerba, E. Alden-Danforth, T. Lectka: Acc. Chem. Res. 2008 41:655.
17. B. List: Chem. Commun. 2006:819.
18. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List: Chem. Rev. 2007 107:5471.
19. G. Lelais, D. W. C. MacMillan: Aldrichimica Acta 2006 39:79.
20. A. Erkkilä, I. Majander, P. M. Pihko: Chem. Rev. 2007 107:5416.
21. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen: Angew. Chem., Int. Ed. 2005 44:794.
22. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji: Angew. Chem., Int. Ed. 2005 44:4212.
23. A. Mielgo, C. Palomo: Chem.–Asian J. 2008 3:922.
24. K. L. Jensen, G. Dickmeiss, H. Jiang, L. Albrecht, K. A. Jorgensen: Acc. Chem. Res. 2012 45:248.
25. H. Hiemstra, H. Wynberg: J. Am. Chem. Soc. 1981 103:417.
26. A. Lattanzi: Chem. Commun. 2009:1452.
27. Aziridines and Epoxides in Organic Synthesis, ed. A. K. Yudin, Wiley-VCH, Weinheim, 2006
28. Modern Oxidations Methods, ed. J. E. Bäckvall, Wiley-VCH, Weinheim, 2004
29. O. A. Wong, Y. Shi: Chem. Rev. 2008 108:3958.
30. K. Matsumoto and T. Katsuki, in Catalytic Asymmetric Synthesis, ed. I. Ojima, Wiley-VCH, New York, 2010, p. 849.
31. R. Irie, K. Noda, Y. Ito, N. Matsumoto, T. Katsuki: Tetrahedron Lett. 1990 31:7345.
32. E. N. Jacobsen, W. Zhang, A. R. Muci, J. R. Ecker, L. Deng: J. Am. Chem. Soc. 1991 113:7063.
33. T. Katsuki, K. B. Sharpless: J. Am. Chem. Soc. 1980 102:5974.
34. A. Lattanzi, Catalytic Asymmetric Conjugate Reactions, ed. A. Córdova, Wiley-VCH, Weinheim, 2010, ch. 9
35. M. Marigo, G. Franzén, T. B. Poulsen, W. Zhuang, K. A. Jørgensen: J. Am. Chem. Soc. 2005 127:6964.
36. X. Wang, B. List: Angew. Chem., Int. Ed. 2008 47:1119.
37. X. Wang, C. M. Reisinger, B. List: J. Am. Chem. Soc. 2008 130:6070.
38. H. Kakei, R. Tsuji, T. Ohshima, M. Shibasaki: J. Am. Chem. Soc. 2005 127:8962.
39. T. Nemoto, H. Kakei, V. Gnanadesikan, S. Tosaki, T. Ohshima, M. Shibasaki: J. Am. Chem. Soc. 2002 124:14544.
40. A. Lattanzi: Org. Lett. 2005 7:2579.
41. A. Lattanzi: Adv. Synth. Catal. 2006 348:339.
42. C. Zheng, Y. Li, Y. Yang, H. Wang, H. Cui, J. Zhang, G. Zhao: Adv. Synth. Catal. 2009 351:1685.
43. D. J. Mature, T. K. Jones, L. C. Xavier, T. J. Blacklock, R. A. Reamer, J. J. Mohan, E. T. T. Turner Jones, K. Hoogsteen, M. W. Baum, E. J. J. Grabowski: J. Org. Chem. 1991 56:751.
44. D. Bailey, D. O'Hagan, M. Tavash: Tetrahedron: Asymmetry 1997 8:149.
45. A. Russo, A. Lattanzi: Org. Biomol. Chem. 2010 8:2633.
46. C. Yoakim, W. W. Ogilvie, N. Goudreau, J. Naud, B. Haché, J. A. O'Meara, M. G. Cordingley, J. Archambault, P. W. White: Bioorg. Med. Chem. Lett. 2003 13:2539.
47. A. Lattanzi, A. Russo, P. Rizzo, G. Monaco, R. Zanasi: Chirality 2010 22:E130.
48. B.-F. Sun, R. Hong, Y.-B. Kang, L. Deng: J. Am. Chem. Soc. 2009 131:10384.
49. C. De Fusco, C. Tedesco, A. Lattanzi: J. Org. Chem. 2011 76:676.
50. C. Palumbo, G. Mazzeo, A. Mazziotta, A. Gambacorta, M. A. Loreto, A. Migliorini, S. Superchi, D. Tofani, T. Gasperi: Org. Lett. 2011 13:6248.
51. K. C. Nicolau, P. B. Rao, J. L. Hao, M. V. Reddy, G. Rassias, X. H. Huang, D. Y. K. Chen, S. A. Snyder: Angew. Chem., Int. Ed. 2003 42:1753.
52. A. Dandia, R. Singh, M. Saha, A. Shivpuri: Pharmazie 2002 57:602.
53. A. Capobianco, A. Russo, A. Lattanzi, A. Peluso: Adv. Synth. Catal. 2012 354:2789.
54. E. Weitz, A. Scheffer: Ber. Dtsch. Chem. Ges. 1921 54:2327.
55. D. Almaşi, D. A. Alonso, C. Nájera: Tetrahedron: Asymmetry 2007 18:299.
56. S. Sulzer-Mossé, A. Alexakis: Chem. Commun. 2007:3123.
57. Y. Zhang, W. Wang: Catal. Sci. Technol. 2012 2:42.
58. A. Lattanzi: Tetrahedron: Asymmetry 2006 17:837.
59. A. Russo, A. Capobianco, A. Perfetto, A. Lattanzi, A. Peluso: Eur. J. Org. Chem. 2011:1922.
60. A. Lattanzi, C. De Fusco, A. Russo, A. Poater, L. Cavallo: Chem. Commun. 2012 48:1650.
61. J. Pietruzka: Chem. Rev. 2003 103:1051.
62. D. Y.-K. Chen, R. H. Pouwer, J.-A. Richard: Chem. Soc. Rev. 2012 41:4631.
63. C. A. Carson, M. A. Kerr: Chem. Soc. Rev. 2009 38:3051.
64. F. De Simone, J. Waser: Synthesis 2009:3353.
65. A. Reichelt, S. F. Martin: Acc. Chem. Res. 2006 39:433.
66. Z. D. Crane, P. J. Nichols, T. Sammachia, P. J. Stengel: J. Org. Chem. 2011 76:277.
67. H. Pellissier: Tetrahedron 2008 64:7041.
68. S. H. McCooey, T. McCabe, S. J. Connon: J. Org. Chem. 2006 71:7494.
69. A. Russo, A. Lattanzi: Tetrahedron: Asymmetry 2010 21:1155.
70. A. Russo, S. Meninno, C. Tedesco, A. Lattanzi: Eur. J. Org. Chem. 2011:5096.
71. J. Christoffers, A. Baro: Adv. Synth. Catal. 2005 347:1473.
72. M. Bella, T. Gasperi: Synthesis 2009:1583.
73. J. P. Das, I. Marek: Chem. Commun. 2011 47:4593.
74. M. Marigo, K. A. Jørgensen: Chem. Commun. 2006:2001.
75. A. M. R. Smith, K. K. Hii: Chem. Rev. 2011 111:1637.
76. A. Russo, C. De Fusco, A. Lattanzi: RSC Adv. 2012 2:385.
77. S. Sobhani, D. Fielenbach, M. Marigo, T. C. Wabnitz, K. A. Jørgensen: Chem.–Eur. J. 2005 11:5689.
78. L. Fang, A. Lin, H. Hu, C. Zhu: Chem.–Eur. J. 2009 15:7039.
79. A. Lin, L. Fang, X. Zhu, C. Zhu, Y. Cheng: Adv. Synth. Catal. 2011 353:545.
80. C. Schneider: Angew. Chem., Int. Ed. 2009 48:2082.
81. Z. Li, M. Fernández, E. N. Jacobsen: Org. Lett. 1999 1:1611.
82. T. Mita, I. Fijimori, R. Wada, J. Wen, M. Kanai, M. Shibasaki: J. Am. Chem. Soc. 2005 127:11252.
83. E. B. Rowland, G. B. Rowland, E. Rivera-Otero, J. C. Antilla: J. Am. Chem. Soc. 2007 129:12084.
84. Z.-B. Luo, X.-L. Hou, L.-X. Dai: Tetrahedron: Asymmetry 2007 18:443.
85. T. A. Moss, D. R. Fenwick, D. J. Dixon: J. Am. Chem. Soc. 2008 130:10076.
86. Y. Zhang, C. W. Kee, R. Lee, X. Fu, J. Y.-T. Soh, E. M. F. Loh, K.-W. Huang, C.-H. Tan: Chem. Commun. 2011 47:3897.
87. A. Lattanzi, G. Della Sala: Eur. J. Org. Chem. 2009:1845.
88. S. Karlsson, H.-E. Högberg: Tetrahedron: Asymmetry 2002 13:923.
89. C. Zhong, Y. Chen, J. L. Petersen, N. G. Akhmedov, X. Shi: Angew. Chem., Int. Ed. 2009 48:1279.
90. Y. Lee, S.-G. Kim: Bull. Korean Chem. Soc. 2011 32:311.
91. B. List, R. A. Lerner, C. F. Barbas III: J. Am. Chem. Soc. 2000 122:2395.
92. B. M. Trost, C. S. Brindle: Chem. Soc. Rev. 2010 39:1600.
93. Y. Hayashi, T. Itoh, S. Aratake, H. Ishikawa: Angew. Chem., Int. Ed. 2008 47:2082.
94. T. Itoh, H. Ishikawa, Y. Hayashi: Org. Lett. 2009 11:3854.
95. T. Urushima, Y. Yasui, H. Ishikawa, Y. Hayashi: Org. Lett. 2010 12:2966.
96. Y. Hayashi, Y. Yasui, T. Kawamura, M. Kojima, H. Ishikawa: Synlett 2011:485.
97. Y. Hayashi, Y. Yasui, M. Kojima, T. Kawamura, H. Ishikawa: Chem. Commun. 2012 48:4570.
98. A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan: Angew. Chem., Int. Ed. 2004 43:2152.
99. Y. Hayashi, Y. Yasui, T. Kawamura, M. Kojima, H. Ishikawa: Angew. Chem., Int. Ed. 2011 50:2804.
100. H. Pellissier: Tetrahedron 2009 65:2839.
101. P. Merino, E. Marques-Lopez, T. Tejero, R. P. Herrera: Synthesis 2010:1.
102. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan: J. Am. Chem. Soc. 2000 122:4243.
103. C. Zheng, Y. Lu, J. Zhang, X. Chen, Z. Chai, W. Ma, G. Zhao: Chem.–Eur. J. 2010 16:5853.
104. X. Cai, C. Wang, J. Sun: Adv. Synth. Catal. 2012 354:359.
105. U. Grošelj, D. Seebach, D. M. Badine, W. B. Schweizer, A. K. Beck, I. Krossing, P. Klose, Y. Hayashi: Helv. Chim. Acta 2009 92:1225.
106. M. B. Schmid, K. Zeitler, R. M. Gschwind: Chem. Sci. 2011 2:1793.
107. J. Burés, A. Armstrong, D. G. Blackmond: J. Am. Chem. Soc. 2012 134:6741.