Asymmetric catalytic routes to dialkyl peroxides and oxaziridines

ACS Catalysis

Volumn 4, Issue 4, 2014, Pages 1234-1245

  Della Sala, Giorgio ^a   Lattanzi, Alessandra ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

asymmetric synthesis; desymmetrization; dialkyl peroxides; kinetic resolution; organocatalysis; oxaziridines; transition metal catalysis

Indexed keywords

ASYMMETRIC SYNTHESIS; DESYM-METRIZATION; KINETIC RESOLUTION; ORGANOCATALYSIS; OXAZIRIDINES; TRANSITION METAL CATALYSIS;

CATALYSIS; CYCLOADDITION; OXIDATION; REACTION KINETICS;

PEROXIDES;

EID: 84898065272     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs500132m     Document Type: Review

References (111)

1. Ojima, I., Ed.; Catalytic Asymmetric Synthesis, 3 rd ed.; John Wiley: Hoboken, NJ, 2010; pp 839-890.
2. Katsuki, T. Science of Synthesis, Water in Chemistry; Thieme: Stuttgart, 2012; pp 53-94.
3. Ager, D. J., Ed.; Handbook of Chiral Chemicals, 2 nd ed.; Taylor & Francis: Boca Raton, 2006; pp 123-146.
4. Casteel, D. A. Nat. Prod. Rep. 1999, 16, 55-73
5. Tang, Y.; Dong, Y.; Vennerstrom, J. L. Med. Res. Rev. 2004, 24, 425-448
6. Rappoport, Z., Ed.; The Chemistry of Peroxides; Wiley: Chichester, U.K., 2006; Vol. 2.
7. Adam, W., Ed.; Peroxide Chemistry; Wiley-VCH: Weinheim, Germany, 2000.
8. Staben, S. T.; Linghu, X.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 12658-12659
9. Wiegand, C.; Herdtweck, E.; Bach, T. Chem. Commun. 2012, 48, 10195-10197
10. Priest, J.; Longland, M. R.; Elsegood, M. R. J.; Kimber, M. C. J. Org. Chem. 2013, 78, 3476-3481
11. Davis, F. A. J. Org. Chem. 2006, 71, 8993-9003
12. Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919-934
13. Troisi, L.; De Lorenzis, S.; Fabio, M.; Rosato, F.; Granito, C. Tetrahedron: Asymmetry 2008, 19, 2246-2251
14. Troisi, L.; Caccamese, S.; Pilati, T.; Videtta, V.; Rosato, F. Synthesis 2010, 3211-3216
15. Aubé, J. Chem. Soc. Rev. 1997, 26, 269-277
16. Davis, F. A.; Weismiller, M. C. J. Org. Chem. 1990, 55, 3715-3717
17. Davis, F. A.; ThimmaReddy, R.; Weismiller, M. C. J. Am. Chem. Soc. 1989, 111, 5964-5965
18. Davis, F. A.; Thimma Reddy, R.; Han, W.; Carroll, P. J. J. Am. Chem. Soc. 1992, 114, 1428-1437
19. Xu, X.-X.; Dong, H.-Q. J. Org. Chem. 1995, 60, 3039-3044
20. Dussault, P. H.; Woller, K. R. J. Am. Chem. Soc. 1997, 119, 3824-3825
21. ONeill, P. M.; Searle, N. L.; Raynes, K. J.; Maggs, J. L.; Ward, S. A.; Storr, R. C.; Park, B. K.; Posner, G. H. Tetrahedron Lett. 1998, 39, 6065-6068
22. Xu, C.; Raible, J. M.; Dussault, P. H. Org. Lett. 2005, 7, 2509-2511
23. Dai, P.; Dussault, P. H. Org. Lett. 2005, 7, 4333-4335
24. Griesbeck, A. G.; Raabe, A. Synlett 2009, 1514-1516
25. Rubush, D. M.; Morges, M. A.; Rose, B. J.; Thamm, D. H.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 13554-13557
26. Wu, Y. Acc. Chem. Res. 2002, 35, 255-259
27. Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2003, 20, 1-48
28. Posner, G. H.; ONeil, P. M. Acc. Chem. Res. 2004, 37, 397-404
29. Nicolaou, K. C.; Lu, M.; Totokotsopoulos, S.; Heretsch, P.; Giguère, D.; Sun, Y.-P.; Sarlah, D.; Nguyen, T. H.; Wolf, I. C.; Smee, D. F.; Day, C. W.; Bopp, S.; Winzeler, E. A. J. Am. Chem. Soc. 2012, 134, 17320-17332
30. Meshnick, S. R.; Jefford, C. W.; Posner, G. H.; Avery, M. A.; Peters, W. Parasit. Today 1996, 12, 79-82
31. Robert, A.; Dechy-Cabaret, O.; Cazelles, J.; Meunier, B. Acc. Chem. Res. 2002, 35, 167-174
32. For a review on endoperoxides, see: Balci, M. Chem. Rev. 1981, 81, 91-108
33. Adam, W.; Peters, E.-M.; Peters, K.; Prein, M.; von Schnering, H. G. J. Am. Chem. Soc. 1995, 117, 6686-6690
34. Dussault, P. H.; Han, Q.; Sloss, D. G.; Symonsbergen, D. J. Tetrahedron 1999, 55, 11437-11454
35. Adam, W.; Balci, M.; Kilic, H. J. Org. Chem. 2000, 65, 5926-5931
36. Kurbanog lu Balci M. Tetrahedron 2010 66, 3485-3489
37. Baran, A.; Cambul, S.; Nebliogu, M.; Balci, M. J. Org. Chem. 2012, 77, 5086-5097
38. Wojaczyńska, E.; Turowska-Tyrk, I. Tetrahedron: Asymmetry 2013, 24, 1247-1251
39. Adam, W.; Rios, A. J. Chem. Soc. D 1971, 822-823
40. Xianming, H.; Kellogg, R. M. Tetrahedron: Asymmetry 1995, 6, 1399-1408
41. Dussault, P. H.; Trullinger, T. K.; Noor-e-Ain, F. Org. Lett. 2002, 4, 4591-4593
42. Marson, C. M.; Khan, A.; Porter, R. A. J. Org. Chem. 2001, 66, 4771-4775
43. Marson, C. M.; McGregor, J.; Khan, A. J. Org. Chem. 1998, 63, 7833-7839
44. Weitz, E.; Scheffer, A. Chem. Ber. 1921, 54, 2344
45. Schulz, M.; Kluge, R.; Gelalcha, F. G. Tetrahedron: Asymmetry 1998, 9, 4341-4360
46. Kharasch, M. S.; Pauson, P.; Nudenberg, W. J. Org. Chem. 1953, 18, 322-327
47. Enantioselective Organocatalysis: Reactions and Experimental Procedures; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, 2007.
48. Asymmetric Organocatalysis; List, B., Ed.; Springer: Berlin, 2010.
49. Buckley, B. R.; Neary, S. P. Organocatalysed Asymmetric Oxidation Reactions. In Enantioselective Organocatalysed Reactions I; Mahrwald, R., Ed.; Springer: Dordrecht, 2011, pp 1-41.
50. Russo, A.; De Fusco, C.; Lattanzi, A. ChemCatChem 2012, 4, 901-916
51. Lu, X.; Liu, Y.; Sun, B.; Cindric, B.; Deng, L. J. Am. Chem. Soc. 2008, 130, 8134-8135
52. Reisinger, C. M.; Wang, X.; List, B. Angew. Chem., Int. Ed. 2008, 47, 8112-8115
53. Lifchits, O.; Mahlau, M.; Reisinger, C. M.; Lee, A.; Farès, C.; Polyak, I.; Gopakumar, G.; Thiel, W.; List, B. J. Am. Chem. Soc. 2013, 135, 6677-6693
54. For the first asymmetric synthesis of 1,2-dioxolane-3-acetic acid derivatives, see: Dai, P.; Trullinger, T. K.; Liu, X.; Dussault, P. H. J. Org. Chem. 2006, 71, 2283-2292
55. Russo, A.; Lattanzi, A. Adv. Synth. Catal. 2008, 350, 1991-1995
56. Feng, X.; Yuan, Y.-Q.; Cui, H.-L.; Jiang, K.; Chen, Y.-C. Org. Biomol. Chem. 2009, 3660-3662
57. Ratnikov, M. O.; Farkas, L. E.; Doyle, M. P. J. Org. Chem. 2012, 77, 10294-10303
58. Akiyama, T. Chem. Rev. 2007, 107, 5744-5758
59. Terada, M. Synthesis 2010, 1929-1982
60. Rebek, Jr.; Mc Cready, R. J. Am. Chem. Soc. 1980, 102, 5602-5605
61. Machin, P. J.; Sammes, P. G. J. Chem. Soc. Perkin Trans. 1 1976, 628-634
62. Kienle, M.; Argyrakis, W.; Baro, A.; Laschat, S. Tetrahedron Lett. 2008, 49, 1971-1974
63. Blumenthal, H.; Liebscher, J. ARKIVOC 2009, xi, 204-220
64. Zheng, W.; Wojtas, L.; Antilla, J. C. Angew. Chem., Int. Ed. 2010, 49, 6589-6591
65. Pramanik, S.; Ghorai, P. Org. Lett. 2013, 15, 3832-3835
66. Kornblum, N.; DeLaMare, H. E. J. Am. Chem. Soc. 1951, 73, 880-881
67. Emmons, W. D. J. Am. Chem. Soc. 1956, 78, 6208-6209
68. Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703-5742
69. Davis, F. A.; Thimma Reddy, R. Oxaziridines and Oxazirines. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 1; pp 365-413.
70. Davis, F. A; Chen, B.-C.; Zhou, P. Oxaziridines and Oxazirines. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008; Vol. 1, pp 559-622.
71. Buglioni, L. Synlett 2013, 2773-2774
72. Mishra, J. K. Synlett 2005, 543-544
73. Petrov, V. A.; Resnati, G. Chem. Rev. 1996, 96, 1809-1823
74. Vidal, J.; Damestoy, S.; Guy, L.; Hannachi, J.-C.; Aubry, A.; Collet, A. Chem.-Eur. J. 1997, 3, 1691-1709
75. Andreae, S.; Schmitz, E. Synthesis 1991, 327-341
76. Bjørgo, J.; Boyd, D. R. J. Chem. Soc., Perkin Trans. 2 1973, 1575-1577
77. Montanari, F.; Moretti, I.; Torre, G. J. Chem. Soc. Chem. Commun. 1969, 1086-1087
78. Jennings, W. B.; Watson, S. P.; Tolley, M. S. J. Am. Chem. Soc. 1987, 109, 8099-8100
79. Armstrong, A.; Edmonds, I. D.; Swarbrick, M. E. Tetrahedron Lett. 2003, 44, 5335-5338
80. Armstrong, A.; Edmonds, I. D.; Swarbrick, M. E. Tetrahedron Lett. 2005, 46, 2207-2210
81. Bohé, L.; Lusinchi, M.; Lusinchi, X. Tetrahedron 1999, 55, 141-154
82. (a) Bohé, L.; Lusinchi, M.; Lusinchi, X. Tetrahedron 1999, 55, 155-166
83. Akhatou, A.; Rahimi, M.; Cheboub, K.; Ghosez, L.; Hanquet, G. Tetrahedron 2007, 63, 6232-6240
84. Davis, F. A.; Jenkins, R. H., Jr.; Awad, S. B.; Stringer, O. D.; Watson, W. H.; Galloy, J. J. Am. Chem. Soc. 1982, 104, 5412-5418
85. Davis, F. A.; Chattopadhyay, S. Tetrahedron Lett. 1986, 27, 5079-5082
86. Carroccia, L.; Fioravanti, S.; Pellacani, L.; Sadun, C.; Tardella, P. A. Tetrahedron 2011, 67, 5375-5381
87. Schoumacker, S.; Hamelin, O.; Téti, S.; Pécaut, J.; Fontecave, M. J. Org. Chem. 2005, 70, 301-308
88. Di Gioia, M. L.; Leggio, A.; Le Pera, A.; Liguori, A.; Siciliano, C. J. Org. Chem. 2005, 70, 10494-10501
89. Davis, F. A.; McCauley, J. P., Jr.; Chattopadhyay, S.; Harakal, M. E.; Towson, J. C.; Watson, W. H.; Tavanaiepour, I. J. Am. Chem. Soc. 1987, 109, 3370-3371
90. Davis, F. A.; ThimmaReddy, R.; McCauley, J. P., Jr.; Przeslawski, R. M.; Harakal, M. E. J. Org. Chem. 1991, 56, 809-815
91. Lattes, A.; Oliveros, E.; Riviére, M.; Belzecki, C.; Mostowicz, D.; Abramskj, W.; Piccinni-Leopardi, C.; Germain, G.; Van Meerssche, M. J. Am. Chem. Soc. 1982, 104, 3929-3934
92. Bulman Page, P. C.; Limousin, C.; Murrell, V. L. J. Org. Chem. 2002, 67, 7787-7796
93. Aubé, J.; Wang, Y. Tetrahedron Lett. 1988, 29, 6407-6408
94. Davis, F. A.; Towson, J. C.; Weismiller, M. C.; Lal, S.; Carroll, P. J. J. Am. Chem. Soc. 1988, 110, 8477-8482
95. Davis, F. A.; Haque, M. S.; Ulatowski, T. G.; Towson, J. C. J. Org. Chem. 1986, 51, 2402-2404
96. Davis, F. A.; Weismiller, M. C.; Lal, G. S.; Chen, B.-C.; Przeslawski, R. M. Tetrahedron Lett. 1989, 30, 1613-1616
97. Davis, F. A.; Kumar, A.; Chen, B.-C. J. Org. Chem. 1991, 56, 1143-1145
98. Verfürth, U.; Ugi, I. Chem. Ber. 1991, 124, 1627-1634
99. Pirkle, W. H.; Rinaldi, P. L. J. Org. Chem. 1977, 42, 2080-2082
100. Forni, A.; Moretti, I.; Torre, G. J. Chem. Soc., Perkin Trans. 2 1987, 699-704
101. Bucciarelli, M.; Forni, A.; Marcaccioli, S.; Moretti, I.; Torre, G. Tetrahedron 1983, 39, 187-192
102. Toda, F.; Tanaka, K. Chem. Lett. 1987, 2283-2284
103. Lykke, L.; Rodríguez-Escrich, C.; Jørgensen, K. A. J. Am. Chem. Soc. 2011, 133, 14932-14935
104. Zhang, T.; He, W.; Zhao, X.; Jin, Y. Tetrahedron 2013, 69, 7416-7422
105. Uraguchi, D.; Tsutsumi, R.; Ooi, T. J. Am. Chem. Soc. 2013, 135, 8161-8164
106. Payne, G. B.; Deming, P. H.; Williams, P. H. J. Org. Chem. 1961, 26, 659-663
107. Payne, G. B. Tetrahedron 1962, 18, 763-765
108. Olivares-Romero, J. L.; Li, Z.; Yamamoto, H. J. Am. Chem. Soc. 2012, 134, 5440-5443
109. Shao, P.-L.; Chen, X.-Y.; Ye, S. Angew. Chem., Int. Ed. 2010, 49, 8412-8416
110. Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2012, 134, 12370-12373
111. Dong, S.; Liu, X.; Zhu, Y.; He, P.; Lin, L.; Feng, X. J. Am. Chem. Soc. 2013, 135, 10026-10029