Synthesis of highly diastereo- and enantiomerically enriched tetracarbonyl(η3-allyl)iron(1+) complexes for allylic substitutions with silyl enol ethers and silyl ketene acetals

Journal of Organometallic Chemistry

Volumn 519, Issue 1-2, 1996, Pages 147-159

  Enders, Dieter ^a   Frank, Udo ^a   Fey, Peter ^a   Jandeleit, Bernd ^a   Lohray, Braj Bhushan ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

6 Oxoenoates; A4 Umpolung; Allylic substitution; Asymmetric synthesis; Chirality transfer; Iron; Planar chirality; Tetracarbonyl( 3 allyl)iron(1+) complex

Indexed keywords

STAPHYLOCOCCUS PHAGE 3A;

EID: 0030602713     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(96)06161-X     Document Type: Article

References (113)

1. General use of transition metals in organic synthesis Hegedus L.S. Organische Synthese mit Übergangsmetallen. 1995;VCH, Weinheim, Germany.
2. Pearson A.J. Trost B.M., Fleming I. Comprehensive Organic Synthesis. 4:1991;663 Pergamon, Oxford.
3. Semmelhack M.F. Trost B.M., Fleming I. Comprehensive Organic Synthesis. 4:1991;517 Pergamon, Oxford.
4. Pike R.D., Sweigart D.A. Synlett. 1990;565.
5. Blystone S.C. Chem. Rev. 89:1989;1663.
6. Consiglio G., Waymouth R.W. Chem. Rev. 89:1989;257.
7. Pearson A.J. Hartley F.R., Patai S. The Chemistry of the Metal-Carbon Bond. 4:1987;889 Wiley, Chichester.
8. Palladium, recent results Anderson P.G., Harden A.H., Tanner D., Norby P.-O. Chem. Eur. J. 1:1995;12.
9. Palladium, recent results Baldwin I.C., Williams J.M.J., Beckett R.P. Tetrahedron: Asymmetry. 6:1995;1515.
10. Palladium, recent results Gamez P., Dunjic B., Fache F., Lamaire M. Tetrahedron: Asymmetry. 6:1995;1109.
11. Palladium, recent results Wimmer P., Widhalm M. Tetrahedron: Asymmetry. 6:1995;657.
12. Palladium, recent results Baldwin I.C., Williams J.M.J., Beckett R.P. Tetrahedron: Asymmetry. 6:1995;679.
13. Palladium, recent results Yamazaki A., Achiva K. Tetrahedron: Asymmetry. 6:1995;51.
14. Palladium, recent results von Matt P., Lloyd-Jones G.C., Minidis A.B.E., Pfaltz A., Macko L., Neuburger M., Zehnder M., Rüegger H., Pregosin P.S. Helv. Chim. Acta. 78:1995;265.
15. Palladium, recent results Dawson G.J., Williams J.M.J. Tetrahedron Lett. 36:1995;461.
16. Palladium, recent results Bolm C., Kaufmann D., Gessler S., Harms K. J. Organomet. Chem. 502:1995;47.
17. Palladium, recent results Trost B.M., Stenkamp D., Pulley S.R. Chem. Eur. J. 1:1995;568.
18. Palladium, recent results Malet R., Moreno-Mañas M., Parella T., Pleixtas R. Organometallics. 14:1995;2463.
19. Palladium, recent results Goux C., Massacret M., Lhoste P., Sinou D. Organometallics. 14:1995;4585.
20. Palladium, recent results Seebach D., Devaquet E., Ernst A., Hayakawa M., Kühnle F.N.M., Schweitzer W.B., Weber B. Helv. Chim. Acta. 78:1995;1636.
21. Palladium, recent results Yoshizaki H., Satoh H., Sato Y., Nakai S., Shibasaki M., Mori M. J. Org. Chem. 60:1995;2061.
22. Palladium, recent results Yamazaki A., Achiwa K. Tetrahedron: Asymmetry. 6:1995;1021.
23. Palladium, recent results Hiroi K., Yamaoka N., Kato F., Oishi K. Tetrahedron Lett. 36:1995;7251.
24. Palladium, recent results Gamez P., Dunjic B., Fache F., Lemaire M. Tetrahedron: Asymmetry. 6:1995;1109.
25. Palladium, recent results Wimmer P., Widhalm M. Tetrahedron: Asymmetry. 6:1995;657.
26. Palladium, recent results Baldwin I.C., Williams J.M.J., Beckett R.P. Tetrahedron: Asymmetry. 6:1995;679.
27. Palladium, recent results Dawson G.J., Williams J.M.J. Tetrahedron Lett. 36:1995;461.
28. Palladium, recent results Knühl G., Sennhenn P., Helmchen G. J. Chem. Soc. Chem. Commun. 1995;1845.
29. Palladium, recent results Dawson G.J., Williams J.M.J., Coote S.J. Tetrahedron: Asymmetry. 6:1995;2535.
30. Palladium, recent results Eichelmann H., Gais H.-J. Tetrahedron: Asymmetry. 6:1995;643.
31. reviews Reiser O. Angew. Chem. 105:1993;576.
32. reviews Reiser O. Angew. Chem. Int. Ed. Engl. 32:1993;547.
33. reviews Frost C.G., Howarth J., Williams J.M.J. Tetrahedron: Asymmetry. 3:1992;1089.
34. reviews Hayashi T. Ojima I. Catalytic Asymmetric Synthesis. 1993;325 VCH, Weinheim, Germany.
35. Nickel Bricout H., Carpentier J.-F., Mortreux A. J. Chem. Soc. Chem. Commun. 1995;1863.
36. Nickel Indolese A.F., Consiglio G. Organometallics. 13:1994;2230.
37. Nickel Consiglio G., Indolese A.F. Organometallics. 10:1991;3425.
38. Nickel Kobayashi Y., Ikeda E. J. Chem. Soc. Chem. Commun. 1994;1789.
39. Nickel Kang S.K., Cho D.G., Park C.H., Namkoong E.Y., Shin J.S. Synth. Commun. 25:1995;1659.
40. Molybdenum Trost B.M., Merlic C.A. J. Am. Chem. Soc. 112:1990;9590.
41. Molybdenum Faller J.W., Mazzieri M.R., Nguyen J.T., Parr J., Tokunaga M. Pure Appl. Chem. 66:1994;1463.
42. Molybdenum Yu R.H., McCallum J.S., Liebeskind L.S. Organometallics. 13:1994;1476.
43. Molybdenum Dvorak D., Stary I., Kocovsky P. J. Am. Chem. Soc. 117:1995;6130.
44. Molybdenum Dvorakova H., Dvorak D., Kocovsky P. Tetrahedron Lett. 36:1995;6351.
45. Tungsten Lloyd-Jones G.C., Pfaltz A. Angew. Chem. 107:1995;534.
46. Tungsten Lloyd-Jones G.C., Pfaltz A. Angew. Chem. Int. Ed. Engl. 34:1995;462.
47. Tungsten Frisell H., Åkermark B. Organometallics. 14:1995;534.
48. Tungsten Lehmann J., Lloyd-Jones G.C. Tetrahedron. 51:1995;8863.
49. Ruthenium Kondo T., Ono H., Satake N., Mitsudo T., Watanabe Y. Organometallics. 14:1995;1945.
50. Ruthenium Zhang S.-W., Mitsudo T., Kondo T., Watanabe Y. J. Organomet. Chem. 450:1993;197.
51. Copper Persson E.S.M., van Klaveren M., Grove D.M., Bäckvall J.E., van Koten G. Chem. Eur. J. 1:1995;351.
52. Copper van Klaveren M., Persson E.S.M., del Vilar A., Grove D.M., Bäckvall J.-E., van Koten G. Tetrahedron Lett. 36:1995;3059.
53. Copper Flemming S., Kabbara J., Nickisch K., Westermann J., Mohr J. Synlett. 1995;183.
54. Copper Ibuka T., Nakai K., Habashita H., Hotta Y., Fujii N., Mimura N., Yamamoto Y. Angew. Chem. 106:1994;693.
55. Copper Ibuka T., Nakai K., Habashita H., Hotta Y., Fujii N., Mimura N., Yamamoto Y. Angew. Chem. Int. Ed. Engl. 33:1994;652.
56. Iron Whitesides T.H., Arhart R.W., Slaven R.W. J. Am. Chem. Soc. 95:1973;5792.
57. Iron Pearson A.J. Tetrahedron Lett. 1975;3617.
58. Iron Salzer A., Hafner A. Helv. Chim. Acta. 66:1983;1774.
59. Iron Nicholas K.M., Landoulis S.J. J. Organomet. Chem. 285:1985;C13.
60. Iron Hafner A., von Philips-born W., Salzer A. Helv. Chim. Acta. 69:1986;1757.
61. Iron Silverman G.S., Strickland S., Nicholas K.M. Organometallics. 5:1986;2117.
62. Iron Dieter J.W., Li Z., Nicholas K.M. Tetrahedron Lett. 28:1987;5415.
63. Iron Li Z., Nicholas K.M. J. Organomet. Chem. 402:1991;105.
64. Iron Yeh M.-P.C., Tau S.-I. J. Chem. Soc. Chem. Commun. 1992;13.
65. Fey P. Dissertation. 1985;University of Bonn.
66. Schmitz T. Dissertation. 1990;Technical University of Aachen.
67. Frank U. Dissertation. 1990;Technical University of Aachen.
68. Enders D., Finkam M. Synlett. 1993;401.
69. Enders D., Finkam M. Liebigs Ann. Chem. 1993;551.
70. Enders D., Jandeleit B., Raabe G. Angew. Chem. 106:1994;2033.
71. Enders D., Jandeleit B., Raabe G. Angew. Chem. Int. Ed. Engl. 33:1994;1949.
72. Enders D., Jandeleit B. Synthesis. 1994;1327.
73. Enders D., Jandeleit B. Liebigs Ann. Chem. 1995;1173.
74. Enders D., Jandeleit B., Prokopenko O.F. Tetrahedron. 51:1995;6273.
75. Enders D., Berg S.v., Jandeleit B. Synlett. 1996;18.
76. D. Enders, P. Fey, T. Schmitz, B.B. Lohray and B. Jandeleit, J. Organomet. Chem., in press.
77. Green J.R., Carrol M.K. Tetrahedron Lett. 32:1991;1141.
78. Gadja C., Green J.R. Synlett. 1992;973.
79. Zhou T., Green J.R. Tetrahedron Lett. 34:1993;4497.
80. Koot W.-J., Hiemstra H., Speckamp W.N. J. Chem. Soc. Chem. Commun. 1993;156.
81. Hopman J.C.P., Hiemstra H., Speckamp W.N. J. Chem. Soc. Chem. Commun. 1995;617.
82. Hopman J.C.P., Hiemstra H., Speckamp W.N. J. Chem. Soc. Chem. Commun. 1995;619.
83. Seebach D. Angew. Chem. 91:1979;259.
84. Seebach D. Angew. Chem. Int. Ed. Engl. 18:1979;239.
85. Hase T.A. Umpoled Synthons. 1987;Wiley, New York.
86. Weiss E., Stark K., Lancaster J.E., Murdoch H.D. Helv. Chim. Acta. 46:1963;288.
87. Dieter J.W., Nicholas K.M. J. Organomet. Chem. 212:1981;107.
88. Reviews Kipphardt H., Enders D. Kontakte (Darmstadt). 2:1985;37.
89. Reviews Ort O. Org. Synth. 65:1987;203.
90. Reviews Herzog H., Scharf H.-D. Synthesis. 1986;420.
91. Reviews Corey E.J., Ensley H. J. Am. Chem. Soc. 97:1975;6907.
92. Pelzer R. Diploma Thesis. 1987;Rheinisch-Westfälische Technische Hochschule, Aachen.
93. Revis A., Hilty T.K. J. Org. Chem. 55:1990;2972.
94. Stang P.J., Mangum M.G., Fox D.P., Haak P. J. Am. Chem. Soc. 96:1974;4562.
95. Ainsworth C., Chen F., Kuo Y.-N. J. Organomet. Chem. 46:1972;59.
96. House H.O., Czuba L.J., Gall M., Olmstead H.D. J. Org. Chem. 34:1969;2324.
97. Reviews Ishmuratov G.Y., Kharisov R.Y., Odinokov V.N., Tolstikov G.A. Russ. Chem. Rev. 64:1995;541.
98. Sterzycki R. Synthesis. 1979;724.
99. Bernardi A., Cardani S., Poli G., Scolastico C. J. Org. Chem. 51:1986;5043.
100. Stephenson G.R., Alexander R.P., Morley C., Howard P.W. Philos. Trans. R. Soc. London Ser. A. 326:1988;545.
101. Zhang W.-Y., Jakiela D.J., Maul A., Knors C., Lauher J.W., Helquist P., Enders D. J. Am. Chem. Soc. 110:1988;4652.
102. Rubio A., Liebeskind L.S. J. Am. Chem. Soc. 115:1993;891.
103. D. Enders, D. Lauscher and R. Kula, unpublished results, 1994.
104. Lombardo L., Taylor R.J.K. Synthesis. 1978;131.
105. Hatekeyama S., Satoh K., Sakurai K., Takano S. Tetrahedron Lett. 28:1987;2173.
106. Review Enders D., Jandeleit B. Acros Org. Acta. 1:1995;59.
107. Braye E.H., Hübel W. Inorg. Synth. 8:1966;179.
108. Tietze L.F., Eicher T. 2nd edn. Reaktionen and Synthesen. 1991;Thieme, Stuttgart.
109. Stadler P.A. Helv. Chim. Acta. 61:1978;1675.
110. Abbott S.J., Jones S.R., Weinman S.A., Bockhoff F.M., McLafferty F.W., Knowles J.R. J. Am. Chem. Soc. 103:1979;4323.
111. Reviews Winterfeldt E. Synthesis. 1975;617.
112. Reviews Solaja B., Serb J. Chem. Soc. 58:1993;155.
113. Jäger V., Wehner V. Angew. Chem. 101:1989;512. Meanwhile the olefation of the lactadehyde derivatives to the enoates 1 could be improved to a synthetically more attractive range(ca.60%).