Enantioselective Baeyer-Villiger oxidations

Current Organic Chemistry

Volumn 8, Issue 12, 2004, Pages 1057-1069

  Mihovilovic, Marko D ^a   Rudroff, Florian ^a   Grötzl, Birgit ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ENANTIOSELECTIVITY; KETONES; OXIDATION; REACTION INTERMEDIATES; STEREOCHEMISTRY; SUSTAINABLE CHEMISTRY;

BAEYER VILLIGER OXIDATION; CARBON-CARBON BOND; CYCLIC KETONES; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; INSERTION PROCESS; ORGANIC CHEMISTRY; OXYGEN INSERTION; PROCESS DEVELOPMENT; ]+ CATALYST;

ORGANOMETALLICS;

CARBON; KETONE; LACTONE; ORGANOMETALLIC COMPOUND; OXYGEN;

BAEYER VILLIGER REACTION; BIOCATALYST; BIOTRANSFORMATION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; METHODOLOGY; NONHUMAN; OPTICS; ORGANIC CHEMISTRY; PRECURSOR; PREDICTION; PURIFICATION; REVIEW; SYNTHESIS;

EID: 3242762987     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272043370159     Document Type: Review

References (111)

1. Baeyer, A.; Villiger, V. Chem. Ber. 1899, 32, 3625-3633.
2. Krow, G.R. Org. React. 1993, 43, 251-798.
3. Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737-750.
4. Criegee, R. Liebigs Ann. Chem. 1948, 560, 127-141.
5. Noyori, R.; Sato, T.; Kobayashi, H. Bull. Chem. Soc. Jpn. 1983, 56, 2661-2679.
6. Mislow, K.; Brenner, J.J. Am. Chem. Soc. 1953, 75, 2318-2322.
7. Bolm, C. In Peroxide Chemistry, Adam, W., Ed.; Wiley-VCH: Weinheim, 2000, 494-510 and references therein.
8. Strukul, G. Angew. Chem. Int. Ed. 1998, 37, 1198-1209.
9. Kamerbeek, N.M.; Janssen, D.B.; van Berkel, W.J.H.; Fraaije, M.W. Adv. Synth. Catal. 2003, 345, 667-678.
10. Mihovilovic, M.D.; Müller, B.; Stanetty, P. Eur. J. Org. Chem. 2002, 3711-3730.
11. Roberts, S.M.; Wan, P. W. H. J. Mol. Catal. B: Enzym. 1998, 4, 111-136.
12. Walsh, C.T.; Chen, Y.-C.J. Angew. Chem. 1988, 100, 342-352.
13. Taschner, M.J.; Black, D.J. J. Am. Chem. Soc. 1988, 110, 6892-6893.
14. Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 30, 3663-3664.
15. Ryerson, C.C.; Ballou, D.P.; Walsh, C. Biochemistry 1982, 21, 2644-2655.
16. Sheng, D.; Ballou, D. P.; Massey, V. Biochemistry 2001, 40, 11156-11167.
17. Willetts, A. Trends Biotechnol. 1997, 15, 55-62.
18. Wichmann, R.; Wandrey, C.; Bückmann, A.F.; Kula, M.-R. Biotechnol. Bioeng. 1981, 23, 2789-2802.
19. Tishkov, V.I.; Galkin, A.G.; Marchenko, G.N.; Tsyganokov, Y.D.; Egorov, H.M. Biotechnol. Appl. Biochem. 1993, 18, 201-207.
20. Willetts, A.J.; Knowles, C. J.; Levitt, M. S.; Roberts, S.M.; Sandey, H.; Shipston, N. F. J. Chem. Soc., Perkin Trans. 1 1991, 1608-1610.
21. Alphand, V.; Archelas, A.; Furstoss, R. J. Org. Chem. 1990, 55, 347-350.
22. Stewart, J.D. Curr. Opinion Biotechnol. 2000, 11, 363-368.
23. Stewart, J.D.; Reed, K. W.; Kayser, M.M. J. Chem. Soc., Perkin Trans. 1 1996, 755-757.
24. Stewart, J.D.; Kieth, W.R.; Zhu, J.; Chen, G.; Kayser, M.M.; J. Org. Chem. 1996, 61, 7652-7653.
25. Kayser, M.M.; Chen, G.; Stewart, J.; J. Org. Chem. 1998, 63, 7103-7106.
26. Chen, G.; Kayser, M.M.; Mihovilovic, M.D.; Mrstik, M.E.; Martinez, C.A.; Stewart, J.D. New J. Chem. 1999, 23, 832.
27. Doig, S. D. O'Sullivan, L.M. Patel, S.; Ward, J.M.; Woodley, J.M. Enzyme Microb. Technol. 2001, 28, 265-274.
28. Simpson, H.D.; Alphand, V.; Furstoss, R. J. Mol. Catal. B: Enzym. 2001, 16, 101-109.
29. Walton, A.Z.; Stewart, J.D. Biotechnol. Prog. 2002, 18, 262-268.
30. Doig, S.D.; Avenell, P.J.; Bird, P.A.; Gallati, P.; Lander, K.S.; Lye, G.J.; Wohlgemuth, T.; Woodley, J.M. Biotechnol. Prog. 2002, 18, 1039-1046.
31. Cheesman, M.J.; Kneller, B.; Kelly, E.J.; Thompson, S.J.; Yeung, C.K.; Eaton, D.L.: Rettie, A.E. Protein Expression Purif. 2001, 21, 81-86.
32. Gutierrrez, M.C.; Sleegers, A.; Simpson, H.D.; Alphand, V.; Furstoss, R. Org. Biol. Chem. 2003, 1, 3500-3506.
33. Fraaije, M.W.; Kamerbeek, N.M.; van Berkel, W.J.H.; Janssen, D. B. FEBS Lett. 2002, 518, 43-47.
34. Van Beilen, J.B.; Mourlane, F.; Seeger, M.A.; Kovac, J.; Li, Z.; Smits, T.H.M.; Fritsche, U.; Witholt, B. Environ. Microbiol. 2003, 5, 174-182.
35. Brzostowicz, P.C.; Gibson, K.L.; Thomas, S.M.; Blasko, M.S.; Rouviere, P.E. J. Bacteriol. 2000, 182, 4241-4248.
36. Brzostowicz, P.; Walters, D.M.; Thomas, S.M.; Nagarajan, V.; Rouviere, P.E. Appl. Environ. Microbiol. 2003, 69, 334-342.
37. Stewart, J.D. Curr. Org. Chem. 1998, 2, 195-216.
38. Donoghue, N. A.; Norris, D. B.; Trudgill, P. W. Eur. J. Biochem. 1976, 63, 175-192.
39. Taschner, M.J.; Black, D.J.; Chen, Q.-Z. Tetrahedron Asymm. 1993, 4, 1387-1390.
40. Stewart, J.D.; Reed, K. W.; Martinez, C. A.; Zhu, J.; Chen, G.; Kayser, M.M. J. Am. Chem. Soc. 1998, 120, 3541-3548.
41. Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc., Perkin Trans. 1 1996, 1867-1872.
42. Berezina, N.; Alphand, V.; Furstoss, R. Tetrahedron Asymm. 2002, 13, 1953-1955.
43. Taschner, M. J.; Peddada, L. J. Chem. Soc., Chem. Commun. 1992, 1384-1385.
44. Mihovilovic, M.D.; Müller, B.; Kayser, M.M.; Stewart, J.D.; Stanetty, P. Synlett 2002, 703-706.
45. Mihovilovic, M.D.; Müller, B.; Kayser, M.M.; Stewart, J.D.; Fröhlich, J.; Stanetty, P.; Spreitzer, H. J. Mol. Catal. B. Enzym. 2001, 11, 349-353.
46. Mihovilovic, M.D.; Rudroff, F.; Kandioller, W.; Grötzl, B.; Stanetty, P.; Spreitzer, H. Synlett. 2003, 1973-1976.
47. Mihovilovic, M.D.; Chen, G.; Wang, S.; Kyte, B.; Rochon, F.; Kayser, M.M.; Stewart, J.D. J. Org. Chem. 2001, 66, 733-738.
48. Griffin, M.; Trudgill, P.W. Eur. J. Biochem. 1976, 63, 199-209.
49. Iwaki, H.; Hasegawa, Y.; Lau, P.C.K.; Wang, S.; Kayser, M.M. Appl. Environ. Microbiol. 2002, 68, 5681-5684.
50. Bes, M.T.; Villa, R.; Roberts, S.M.; Wan, P.W.H.; Willetts, A.J. J. Mol. Catal. B: Enzym. 1996, 1, 127-134.
51. Wang, S.; Kayser, M.M.; Iwaki, H.; Lau, P.C.K. J. Mol. Catal. B: Enzym. 2003, 22, 211-218.
52. Mihovilovic, M.D.; Müller, B.; Schulze, A.; Stanetty, P.; Kayser, M.M. Eur. J. Org. Chem. 2003, 2243-2249.
53. Mihovilovic, M. D.; Rudroff, F.; Müller, B.; Stanetty, P. Bioorg. Med. Chem Lett. 2003, 13, 1479-1482.
54. Jones, K.H.; Smith, R.T.; Trudgill, P.W. J. Gen. Microbiol. 1993, 139, 797-805.
55. Grogan, G.; Roberts, S.; Wan, P.; Willetts, A.J. Biotechnol. Lett. 1993, 15, 913-918.
56. Rheinwald, J.G.; Chakrabarty, A.M.; Gunsalus, I.C. Proc. Nat. Acad. Sci. USA 1973, 70, 885-889.
57. Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P.F.; Roberts, S.M.; Willetts, A.J.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans. 1 1995, 2527-2528.
58. Alphand, V.; Mazzini, C.; Lebreton, J.; Furstoss, R. J. Mol. Catal. B: Enzym. 1998, 5, 219-221.
59. Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. J. Org. Chem. 1997, 62, 5215-5218.
60. Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 1195-1196.
61. Mihovilovic, M.D.; Müller, B.; Kayser, M.M.; Stanetty, P. Synlett. 2002, 700-702.
62. Mihovilovic, M.D.; Rudroff, F.; Grötzl, B.; Mach, R. unpublished results.
63. Taschner, M.J.; Aminbhavi, A.S. Tetrahedron Lett. 1989, 30, 1029-1032.
64. Yokokawa, F.; Hamada, Y.; Shioiri, T. Chem. Commun. 1996, 871-872.
65. Boeckmann, R.K.; Starrett, J.E.; Nickell, D.G.; Sum, P.-E. J. Am. Chem. Soc. 1986, 108, 5549-5559.
66. Neukom, C.; Richardson, D.P.; Myerson, J.H.; Bartlett, P.A. J. Am. Chem. Soc. 1986, 108, 5559-5568.
67. DeShong, P.; Ramesh, S.; Elango, V.; Perez, J. J. Am. Chem. Soc. 1985, 107, 5219-5224.
68. Schlessinger, R.H.; Berberwitz, G.R.; Lin, P. J. Am. Chem. Soc. 1985, 107, 1777-1778.
69. Martin, S.F.; Gluchowski, C.; Campbell, C.L.; Chapman, R.C. J. Org. Chem. 1984, 49, 2512-2513.
70. Ziegler, F.E.; Wester, R.T. Tetrahedron Lett. 1984, 25, 617-620.
71. Ziegler, F.E.; Thottathil, J.K. Tetrahedron Lett. 1981, 22, 4883-4886.
72. Ireland, R.F.; Wuts, P.G.; Ernst, B. J. Am. Chem. Soc. 1981, 103, 3205-3207.
73. Duchamp, D.J.; Branfman, A.R.; Button, A.C.; Rinehart, K.L. J. Am. Chem. Soc. 1973, 95, 4077-4078.
74. Adger, B.; Bes, M. T.; Grogan, G.; McCague, R.; Pedragosa-Moreau, S.; Roberts, S.M.; Villa, R.; Wan. P. W. H.; Willetts, A.J. J. Chem. Soc., Chem. Commun. 1995, 1563-1564.
75. Adger, B.; Bes, M.T.; Grogan, G.; McCague, R.; Podragosa-Moreau, S.; Roberts, S.M.; Villa, R.; Wan, P.W.H.; Willetts, A.J. Bioorg. Med. Chem. 1997, 5, 253-261.
76. Adger, B.M.; McCague, R.; Roberts, S.M. Int. Pat. Appl. WO 96/38437 1996, Chem. Abstr. 126: 89208.
77. Alphand, V.; Furstoss, R. Tetrahedron Asymm. 1992, 3, 379-382.
78. Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 30, 3663-3664.
79. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145-160.
80. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1996, 37, 1011-1014.
81. Andrau, L.; Lebreton, J.; Viazzo, P.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 825-826.
82. Kelly, D.R.; Knowles, C.J.; Mahdi, J.G.; Taylor, I.N.; Wright, M.A. J. Chem. Soc., Chem. Commun. 1995, 729-730.
83. Kelly, D.R.; Knowles, C.J.; Mahdi, T.G.; Wright, M.A.; Taylor, I.N.; Hibbs, D.E.; Hursthouse, M.B.; Mish'al, A.K.; Roberts, S.M.; Wan, P.W.H.; Grogan, G.; Willets, A.J. J. Chem. Soc., Perkin Trans. 1 1995, 2057-2066.
84. Francisco, W.A.; Abu-Soud, H.M.; Topgi, R.; Baldwin, T.O.; Raushel, F.M. J. Biol. Chem. 1996, 271, 104-110.
85. Villa, R.; Willetts, A. J. Mol. Catal. B: Enzym. 1997, 2, 193-197.
86. Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem Rev. 1992, 92, 1071-1140.
87. Kirk, O.; Christensen, M.W.; Damhus, T.; Godtfredsen, S.E. Biocatalysis 1994, 11, 65-77.
88. Lemoult, S.C.; Richardson, P.F.; Roberts, S.M. J. Chem. Soc. Perkin Trans. 1 1995, 89-91.
89. Pchelka, B.K.; Gelo-Pujic, M.; Guibe-Jampel, E. J. Chem. Soc. Perkin Trans. 1 1998, 2625-2627.
90. Carlqvist, P.; Eklund, R.; Hult, K.; Brinck, T. J. Mol. Model, 2003, 9, 164-171.
91. Gusso, A.; Baccin, C.; Pinna, R.; Strukul, G. Organometallics 1994, 13, 3442-3451.
92. Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew Chem. 1994, 106, 1944-1946.
93. Strukul, G.; Varagnolo, A.; Pinna, F. J. Mol. Catal. A: Chem. 1997, 117, 413-423.
94. Paneghetti, C.; Gavagnin, R.; Pinna, F.; Strukul, G. Organometallics 1999, 18, 5057-5065.
95. Gavagnin, R.; Cataldo, M.; Pinna, R.; Strukul, G. Organometallics 1998, 17, 661-667.
96. Ito, K.; Ishii, A.; Kuroda, T.; Katsuki, T. Synlett 2003, 643-646.
97. Uchida, T.; Katsuki, T. Helv. Chim. Acta 2002, 85, 3078-3089.
98. Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481-4485.
99. Bolm, C.; Schlingloff, G.; Weickhardt, K. Tetrahedron Lett. 1993, 34, 3405-3408.
100. Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247-1248.
101. Bolm, C.; Luong, K.K.; Schlingloff, G. Synlett. 1997, 1151-1152.
102. Shinohara, T.; Fujioka, S.; Kotsuki, H. Heterocycles 2001, 55, 237-242.
103. Lopp, M.; Paju, A.; Kanger, T.; Pehk, T. Tetrahedron Lett. 1996, 37, 7583-7586.
104. Bolm, C.; Beckmann, O.; Palazzi, C. Can. J. Chem. 2001, 79, 1593-1597.
105. Bolm, C.; Beckmann, O. Chirality 2000, 12, 523-525.
106. Bolm, C.; Beckmann, O.; Cosp, A.; Palazzi, C. Synlett 2001, 1461-1463.
107. Bolm, C.; Beckmann, O.; Kühn, T.; Palazzi, C.; Adam, W.; Rao, P.B.; Saha-Möller, C.R. Tetrahedron Asymm. 2001, 12, 2441-2446.
108. Mazzini, C.; Lebreton, J.; Furstoss, R. J. Org. Chem. 1996, 61, 8-9.
109. Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem. 2002, 114, 2472-2474.
110. Aoki, M.; Seebach, D. Helv. Chim. Acta 2001, 84, 187-207.
111. Sugimura, T.; Fujiwara, Y.; Tai, A. Tetrahedron Lett. 1997, 38, 6019-6022.