Recent progress towards the understanding of metal-salen catalysed asymmetric alkene epoxidation

Topics in Catalysis

Volumn 5, Issue 1-4, 1998, Pages 75-91

  Dalton, Cormac T ^a   Ryan, Kenneth M ^a   Wall, Valerie M ^a   Bousquet, Claudine ^a   Gilheany, Declan G ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Alkene epoxidation; Catalytic asymmetric epoxidation; Chromium salen complexes; Metal salen complexes; Metallaoxetanes; Salicylaldimines; 2+2 cycloaddition

Indexed keywords

EID: 0002715776     PISSN: 10225528     EISSN: None     Source Type: Journal    
DOI: 10.1023/a:1019102003494     Document Type: Article

References (118)

1. Reported as a series of oral presentations at 211th National Meeting of the American Chemical Society, New Orleans, March 24-28th, 1996; ORGN 161: C.T. Dalton and D.G. Gilheany; ORGN 162: K.M. Ryan and D.G. Gilheany; ORGN 163: E.J. Coyne, V.M. Wall and D.G. Gilheany; ORGN 164: C. Bousquet and D.G. Gilheany; ORGN 165: D.G. Gilheany.
2. (a) E.G. Lewars, in: Comprehensive Heterocyclic Chemistry, Vol. 7, eds. A.R. Katritsky and C.W. Rees (Pergamon, Oxford, 1984) ch. 5.05, pp. 95-129;
3. (b) A.S. Rao, in: Comprehensive Organic Synthesis, Vol. 7, eds. B.M. Trost and I. Fleming (Pergamon, Oxford, 1991) ch. 3.1, pp. 357-387;
4. (c) for a recent highlight see: A. Gansäuer, Angew. Chem. Int. Ed. Engl. 36 (1987) 2591.
5. R.A. Johnson and K.B. Sharpless, in: Comprehensive Organic Synthesis, Vol. 7, eds. B.M. Trost and I. Fleming (Pergamon, Oxford, 1991) ch. 3.2, pp. 389-436; R.A. Johnson and K.B. Sharpless, in: Catalytic Asymmetric Synthesis, ed. I. Ojima (VCH, New York, 1993) ch. 4.1, pp. 101-158.
6. R.A. Johnson and K.B. Sharpless, in: Comprehensive Organic Synthesis, Vol. 7, eds. B.M. Trost and I. Fleming (Pergamon, Oxford, 1991) ch. 3.2, pp. 389-436; R.A. Johnson and K.B. Sharpless, in: Catalytic Asymmetric Synthesis, ed. I. Ojima (VCH, New York, 1993) ch. 4.1, pp. 101-158.
7. (a) E.N. Jacobsen, in: Catalytic Asymmetric Synthesis, ed. I. Ojima (VCH, New York, 1993) ch. 4.2, pp. 159-202;
8. (b) T. Katsuki, Coord. Chem. Rev. 140 (1995) 189; J. Mol. Catal. A: Chem. 113 (1996) 87;
9. (b) T. Katsuki, Coord. Chem. Rev. 140 (1995) 189; J. Mol. Catal. A: Chem. 113 (1996) 87;
10. (c) for a recent highlight see: T. Linker, Angew. Chem. Int. Ed. Engl. 36 (1997) 2060 and references cited therein.
11. H.B. Henbest, Chem. Soc. Spec. Publ. 19 (1965) 83.
12. J. Rebek and R. McCready, J. Am. Chem. Soc. 102 (1980) 5602.
13. R. Curci, M. Fiorentino and M.R. Serio, J. Chem. Soc., Chem. Commun. (1984) 155.
14. H.B. Kagan, H. Mimoun, C. Mark and V. Schurig, Angew. Chem. Int. Ed. Engl. 18 (1979) 485.
15. F.A. Davis, M.E. Harakal and S.B. Awad, J. Am. Chem. Soc. 105 (1983) 3123.
16. T. Katsuki and K.B. Sharpless, J. Am. Chem. Soc. 102 (1980) 5976.
17. R.M. Hanson and K.B. Sharpless, J. Org. Chem. 51 (1986) 1922.
18. K. Tani, M. Hanasfusa and S. Otsuka, Tetrahedron Lett. 32 (1979) 3017.
19. R. Helder, J.C. Hummelen, R.W.P.M. Laane, J.S. Wieringand and H. Wynberg, Tetrahedron Lett. 21 (1976) 1831.
20. W. Zhang, J.L. Loebach, S.R. Wilson and E.N. Jacobsen, J. Am. Chem. Soc. 112 (1990) 2801.
21. S. Chang, J.M. Galvin and E.N. Jacobsen, J. Am. Chem. Soc. 116 (1994) 6937.
22. R. Irie, K. Noda, Y. Ito, N. Matsumoto and T. Katsuki, Tetrahedron Lett. (1990) 7345.
23. C. Bousquet and D.G. Gilheany, Tetrahedron Lett. (1995) 7739.
24. (a) T. Yamada, K. Imagawa, T. Nagata and T. Mukaiyama, Chem. Lett. (1992) 2231;
25. (b) K. Imagawa, T. Nagata, T. Yamada and T. Mukaiyama, Chem. Lett. (1994) 527;
26. (c) T. Yamada, K. Imagawa, T. Nagata and T. Mukaiyama, Bull. Chem. Soc. Jpn. 67 (1994) 2248.
27. (a) T. Mukaiyama, T. Yamada, T. Nagata and K. Imagawa, Chem. Lett. (1993) 327;
28. (b) T. Nagata, K. Imagawa, T. Yamada and T. Mukaiyama, Inorg. Chim. Acta 220 (1994) 283; T. Nagata, K. Imagawa, T. Yamada and T. Mukaiyama, Chem. Lett. (1994) 1259;
29. (b) T. Nagata, K. Imagawa, T. Yamada and T. Mukaiyama, Inorg. Chim. Acta 220 (1994) 283; T. Nagata, K. Imagawa, T. Yamada and T. Mukaiyama, Chem. Lett. (1994) 1259;
30. (c) T. Nagata, K. Imagawa, T. Yamada and T. Mukaiyama, Bull. Chem. Soc. Jpn. 68 (1995), 1455.
31. (a) Y. Tu, Z.X. Wang and Y. Shi, J. Am. Chem. Soc. 118 (1996) 9806;
32. (b) Z.X. Wang, Y. Tu, M. Frohn and Y. Shi, J. Org. Chem. 62 (1997) 2328.
33. J.T. Groves, T.E. Nemo and R.S. Myers, J. Am. Chem. Soc. 101 (1979) 1032.
34. J.T. Groves and W.J. Kruper, J. Am. Chem. Soc. 101 (1979) 7613.
35. E. Guilmet and B. Meunier, Tetrahedron Lett. 23 (1982) 2449.
36. J.T. Groves and T.E. Nemo, J. Am. Chem. Soc. 105 (1983) 5786.
37. B.M. Lynch and K.H. Pausacker, J. Chem.Soc. (1955) 1525.
38. J.T. Groves and R.S. Myers, J. Am. Chem. Soc. 105 (1983) 5791.
39. B. Meunier, E. Guilmet, M.-E. De Carvalho and R. Poilblanc, J. Am. Chem. Soc. 106 (1984) 6668.
40. J.P. Collman, X. Zhang, V.J. Lee, E.S. Uffelman and J.I. Brauman, Science 261 (1993) 1404 and references cited therein.
41. D. Ostovic and T.C. Bruice, Acc. Chem. Res. 25 (1992) 314 and references therein.
42. J.T. Groves, J. Lee and S.S. Marla, J. Am. Chem. Soc. 119 (1997) 6269.
43. J.T. Groves and M.K. Stern, J. Am. Chem. Soc. 109 (1987) 3812.
44. Search of Gmelin database November 19th (1997).
45. T.L. Sidall, N. Miyaura, J.C. Huffmann and J.K. Kochi, J. Chem. Soc., Chem. Commun. (1983) 1185.
46. K. Srinivasan and J.K. Kochi, Inorg. Chem. 24 (1985) 4671.
47. E.G. Samsel, K. Srinivasan and J.K. Kochi, J. Am. Chem. Soc. 107 (1985) 7606.
48. K. Srinivasan, P. Michaud and J.K. Kochi, J. Am. Chem. Soc. 108 (1986) 2309.
49. D. Feichtinger and D.A. Plattner, Angew. Chem. Int. Ed. Engl. 36 (1997) 1718.
50. J.A. Smegal, B.C. Schardt and C.L. Hill, J. Am. Chem. Soc. 105 (1983) 3510 and references therein.
51. J.D. Koola and J.K. Kochi, Inorg. Chem. 26 (1987) 908.
52. H. Yoon and C.J. Burrows, J. Am. Chem. Soc. 110 (1988) 4087.
53. P. Pfeiffer, W. Christeleit, T. Hesse, H. Pfitzinger and H. Thielert, J. Prakt. Chem. 150 (1938) 261.
54. B. Bosnich, Ace. Chem. Res. 2 (1969) 266.
55. E. Cesarotti, A. Pasini and R. Ugo, J. Chem. Soc., Dalton Trans. (1981) 2147 and ref. cited therein.
56. K. Nakajima, M. Kojima and J. Fujita, Chem. Lett. (1986) 1483.
57. A. Nishinaga, H. Yamato, T. Abe, K. Maruyama and T. Marsuura, Tetrahedron Lett. (1988) 6309.
58. W. Zhang and E.N. Jacobsen, J. Org. Chem. 56 (1991) 2296.
59. R. Irie, Y. Ito and T. Katsuki, Synlett (1991) 265.
60. E.N. Jacobsen, W. Zhang, A.R. Muci, J.R. Ecker and L. Deng, J. Am. Chem. Soc. 113 (1991) 7063.
61. (a) K.J. O'Connor, S.-J. Wey and C.J. Burrows, Tetrahedron Lett. 33 (1992) 1001;
62. (b) D.R. Reddy and E.R. Thornton, J. Chem. Soc., Chem. Commun. (1992) 172;
63. (c) A. Robert, A. Tsapara and B. Meunier, J. Mol. Catal. 85 (1993) 13.
64. (a) T. Schwenkreis and A. Berkessel, Tetrahedron Lett. 34 (1993) 4785;
65. (b) A. Berkessel, M. Frauenkreis, T. Schwenkreis, A. Steinmetz, G. Baum and D. Fenske, J. Mol. Catal. A: Chem. 113 (1996) 321;
66. (c) P. Pietikainen, Tetrahedron Lett. 35 (1994) 941;
67. (d) P. Pietikainen, Tetrahedron Lett. 36 (1995) 319.
68. M.T. Rispens, A. Meetsma and B.L. Feringa, Recl. Trav. Chim. Pays-Bas 113 (1994) 413.
69. (a) C.-W. Ho, W.-C. Cheng, M.-C. Cheng, S.-M. Peng, K.-F. Cheng and C.-M. Che, J. Chem. Soc., Dalton Trans. (1996) 405;
70. (b) I.F.J. Vankelecom, D. Tas, R.F. Parton, V. Van de Vyver and P.A. Jacobs, Angew. Chem. Int. Ed. Engl. 35 (1996) 1346;
71. (c) I. Fernandez, J.R. Pedro and R. de la Salud, Tetrahedron 52 (1996) 12031;
72. (d) B. Rhodes, S. Rowling, P. Tidswell, S. Woodward and S.M. Brown, J. Mol. Catal. A: Chem. 116 (1997) 375.
73. (e) K.G. Rasmussen, D.S. Thomsen and K.A. Jørgensen, J. Chem. Soc. Perkins 1 (1995) 2009.
74. (a) S.-H. Zhao, P.R. Ortiz, B.A. Keys and K.G. Davenport, Tetrahedron Lett. 37 (1996) 2725;
75. (b) R.I. Kureshy, N.H. Khan, S.H.R. Abdi, P. Iyer and A.K. Bhatt, J. Mol. Catal. A: Chem. 120 (1997) 101.
76. (a) D. Bell, M.R. Davies, F.J.L. Finney, G.R. Geen, P.M. Kincey and I.S. Mann, Tetrahedron Lett. 37 (1996) 3895;
77. (b) C.H. Senanayake, G.B. Smith, K.M. Ryan, L.E. Fredenburgh, J. Liu, F.E. Roberts, D.L. Hughes, R.D. Larsen, T.H. Verhoeven and P.J. Reider, Tetrahedron Lett. 37 (1996) 3271.
78. (a) M. Calligaris and L. Randaccio, in: Comprehensive Co-ordination Chemistry, Vol. 2, eds. G. Wilkinson, R.D. Gillard and J.A. McCleverty (Pergamon, Oxford, 1987) ch. 20.1, pp. 715-738;
79. (b) M. Calligaris, G. Nardin and L. Randaccio, Coord. Chem. Rev. 7 (1972) 385;
80. (c) L.F. Larkworthy, K.B. Nolan and P. O'Brien, in: Comprehensive Co-ordination Chemistry, Vol. 3, eds. G. Wilkinson, R.D. Gillard and J.A. McCleverty (Pergamon, Oxford, 1987) ch. 35, pp. 699-969;
81. (d) B. Chiswell and E.D. McKenzie, in: Comprehensive Co-ordination Chemistry, Vol. 4, eds. G. Wilkinson, R.D. Gillard and J.A. McCleverty (Pergamon, Oxford, 1987) ch. 41, pp. 1-122.
82. M. Calligaris, G. Manzini, G. Nardin and L. Randaccio, J. Chem. Soc. Dalton. Trans. (1972) 543.
83. N.S. Finney, P.J. Pospisil, S. Chang, M. Palucki, R.G. Konsler, K.B. Hansen and E.N. Jacobsen, Angew. Chem. Int. Ed. Engl. 36 (1997) 1720, footnote 12.
84. T. Hashihayata, Y. Ito and T. Katsuki, Tetrahedron 53 (1997) 9541.
85. P.O Norrby, C. Linde and B. Åkermark, J. Am. Chem. Soc. 117 (1995) 11035.
86. H. Imanishi and T. Katsuki, Tetrahedron Lett. 38 (1997) 251.
87. T. Hamada, T. Fukuda, H. Imanishi and T. Katsuki, Tetrahedron 52 (1996) 515.
88. K.N. Houk, N.C. DeMello, K. Condroski, J. Fennen and T. Kasuga, in: Electronic Conference on Heterocyclic Chemistry (ECHET96), eds. H.S. Rzepa, J.P. Snyder and C. Leach (The Royal Society of Chemistry, London, June 24 - July 22, 1996), http://www.ch.ic.ac.uk/ectoc/echet96/
89. T. Hashihayata, Y. Ito and T. Katsuki, Synlett (1996) 1079.
90. (a) N. Hosoya, A. Hatakeyama, K. Yanai, H. Fujii, R. Irie and T. Katsuki, Synlett (1993) 641;
91. (b) T. Hamada, R. Irie and T. Katsuki, Synlett (1994) 479.
92. T. Kuroki, T. Hamada and T. Katsuki, Chem. Lett. (1995) 339.
93. N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett (1991) 691.
94. B. Bosnich, N.K. Roberts and P.A. MacNeill, J. Am. Chem. Soc. 103 (1981) 2273.
95. P.-O. Norrby, personal communication.
96. K.B. Sharpless, A.Y. Teranishi and J.E. Bäckvall, J. Am. Chem. Soc. 99 (1977) 3120.
97. Reference 36, footnote 35.
98. H. Fu, G.C. Look, W. Zhang, E.N. Jacobsen and C.H. Wong, J. Org. Chem. 56 (1991) 6497.
99. M. Palucki, P.J. Pospisil, W. Zhang and E.N. Jacobsen, J. Am. Chem. Soc. 116 (1994) 9333.
100. G.X. He and T.C. Bruice, J. Am. Chem. Soc. 113 (1991) 2747.
101. (a) J.P. Collman, J.I. Brauman, B. Meunier, T. Hayashi, T. Kodadek and S.A. Raybuck, J. Am. Chem. Soc. 107 (1985) 2000;
102. (b) J.E. Bäckvall, F. Bokman and M.R.A. Blomberg, J. Am. Chem. Soc. 114 (1992) 534.
103. (a) B. Rihter, S. SriHari, S. Hunter and J. Masnovi, J. Am. Chem. Soc. 115 (1993) 3918;
104. (b) B. Rihter and J. Masnovi, J. Chem. Soc., Chem. Commun. (1988) 35.
105. (a) D.W. Nelson, A. Gypser, P.T. Ho, H.C. Kolb, T. Kondo, H.-L. Kwong, D.V. McGrath, A.E. Rubin, P.-O. Norrby, K.P. Gable and K.B. Sharpless, J. Am. Chem. Soc. 119 (1997) 1840 and references cited therein;
106. (b) K.P. Gable and J.J.J. Juliette, J. Am. Chem. Soc. 118 (1996) 2625 and references cited therein.
107. (a) K.A. Jørgensen and B. Schiøtt, Chem. Rev. 90 (1990) 1483;
108. (b) K.A. Jørgensen, Chem. Rev. 89 (1989) 431;
109. (c) E.J. Corey, M.C. Noe and A. Guzman-Perez, J. Am. Chem. Soc. 117 (1995) 10817 and references cited therein.
110. C. Linde, M. Arnold, P.O. Norrby and B. Åkermark, Angew. Chem. Int. Ed. Engl. 36 (1997) 1723.
111. N.S. Finney, P.J. Pospisil, S. Chang, M. Palucki, R.G. Konsler, K.B. Hansen and E.N. Jacobsen, Angew. Chem. Int. Ed. Engl. 36 (1997) 1720.
112. (a) V. McKee, personal communication;
113. (b) T. Metcalfe, Ph.D. thesis QUB 1998.
114. For a recent report of seven co-ordinate manganese see: S. McCann, M. McCann, M.T. Casey, M. Devereux, V. McKee, P. McMichael and J.G. McCrea, Polyhedon 16 (1997) 4247.
115. D. Mikame, T. Hamada, R. Irie and T. Katsuki, Synlett (1995) 827.
116. T. Katsuki, J. Synth. Org. Chem. Jpn. 53 (1996) 940.
117. C.T. Dalton, A. Daly and D.G. Gilheany, unpublished results.
118. J.G. Hamilton, O.N.D. Mackey, J.J. Rooney and D.G. Gilheany, J. Chem. Soc., Chem. Commun. (1990) 1600.