Synthesis of iridium complexes with new planar chiral chelating phosphinyl-imidazolylidene ligands and their application in asymmetric hydrogenation

Tetrahedron Asymmetry

Volumn 15, Issue 11, 2004, Pages 1693-1706

  Focken, Thilo ^a   Raabe, Gerhard ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

(ETA 4 1,5 CYCLOOCTADIENE) [1 (2,4,6 TRIMETHYLPHENYL) 3 [4 (DIPHENYLPHOSPHINYL)[2.2]PARACYCLOPHAN 12 YLMETHYL]IMIDAZOLIN 2 YLIDENE]IRIDIUM TETRAKIS[3,5 BIS(TRIFLUOROMETHYL)PHENYL]BORATE; (ETA 4 1,5 CYCLOOCTADIENE) [1 (2,6 DIISOPROPYLPHENYL) 3 [4 (DIPHENYLPHOSPHINYL)[2.2]PARACYCLOPHAN 12 YLMETHYL]IMIDAZOLIN 2 YLIDENE]IRIDIUM TETRAKIS[3,5 BIS(TRIFLUOROMETHYL)PHENYL]BORATE; (ETA 4 1,5 CYCLOOCTADIENE) [1 PHENYL 3 [4 (DIPHENYLPHOSPHINYL)[2.2]PARACYCLOPHAN 12 YLMETHYL]IMIDAZOLIN 2 YLIDENE]IRIDIUM TETRAKIS[3,5 BIS(TRIFLUOROMETHYL)PHENYL]BORATE; 3 (4 DIPHENYLPHOSPHINO[2.2]PARACYCLOPHAN 12 YLMETHYL) 1 (2,6 DIISOPROPYLPHENYL)IMIDAZOLIUM BROMIDE; 4,12 DIBROMO[2.2]PARACYCLOPHANE; ALKENE DERIVATIVE; CHELATING AGENT; CYCLOPHANE DERIVATIVE; IMIDAZOLE DERIVATIVE; IRIDIUM COMPLEX; LIGAND; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; HYDROGENATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 2942536406     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.03.047     Document Type: Article

References (112)

1. Öfele K. J. Organomet. Chem. 12:1968;P42
2. Wanzlick H.-W., Schönherr H.-J. Angew. Chem. 80:1968;154. Angew. Chem., Ind. Ed. Engl. 1968, 7, 141
3. Arduengo A.J. III, Harlow R.L., Kline M. J. Am. Chem. Soc. 113:1991;361
4. Arduengo A. III J. Acc. Chem. Res. 32:1999;913
5. For reviews about NHCs and NHC metal complexes, see: Cardin D.J., Cetinkaya B., Lappert M.F. Chem. Rev. 72:1972;545
6. Herrmann W.A., Köcher C. Angew. Chem. 109:1997;2256. Angew. Chem., Int. Ed. Engl. 1997, 36, 2163
7. Bourissou D., Guerret O., Gabbaï F.P., Bertrand G. Chem. Rev. 100:2000;39
8. Herrmann W.A. Angew. Chem. 114:2002;1342. Angew. Chem., Int. Ed. 2002, 41, 1290
9. See also: Herrmann W.A., Öfele K., v. Preysing D., Schneider S.K. J. Organomet. Chem. 687:2003;229. and references cited therein
10. For examples of di-N-heterocyclic carbenes and their metal complexes, see: Douthwaite R.E., Haüssinger D., Green M.L.H., Silcock P.J., Gomes P.T., Martins A.M., Danopoulos A.A. Organometallics. 18:1999;4584
11. Douthwaite R.E., Green M.L.H., Silcock P.J., Gomes P.T. Organometallics. 20:2001;2611
12. Douthwaite R.E., Green M.L.H., Silcock P.J., Gomes P.T. J. Chem. Soc., Dalton Trans. 2002;1386
13. For a recent review about phosphines as ligands in enantioselective hydrogenation, see: Tang W., Zhang X. Chem. Rev. 103:2003;3029
14. Selected references on the use of NHCs in olefin metathesis: Weskamp T., Schattenmann W.C., Spiegler M., Herrmann W.A. Angew. Chem. 110:1998;2631. Angew. Chem., Int. Ed. 1998, 37, 2490
15. Weskamp T., Kohl F.J., Herrmann W.A. J. Organomet. Chem. 582:1999;362
16. Scholl M., Trnka T.M., Morgan J.P., Grubbs R.H. Tetrahedron Lett. 40:1999;2247
17. Scholl M., Ding S., Lee C.W., Grubbs R.H. Org. Lett. 1:1999;953
18. Huang J., Schanz H.Z., Stevens E.D., Nolan S.P. Organometallics. 18:1999;5375
19. Fürstner A., Ackermann L., Gabor B., Goddard R., Lehmann C.W., Mynott R., Stelzer F., Thiel O.R. Chem. Eur. J. 7:2001;3236
20. Trnka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18
21. Sanford M.S., Love J.A., Grubbs R.H. J. Am. Chem. Soc. 123:2001;6543
22. Wakamatsu H., Blechert S. Angew. Chem. 114:2002;2509. Angew. Chem., Int. Ed. 2002, 41, 2403
23. Connon S.J., Dunne A.M., Blechert S. Angew. Chem. 114:2002;3989. Angew. Chem., Int. Ed. 2002, 41, 3835
24. Choi T.-L., Rutenberg M., Grubbs R.H. Angew. Chem. 114:2002;3995. Angew. Chem., Int. Ed. 2002, 41, 3839
25. See also Ref. [3d]
26. Connon S.J., Rivard M., Zaja M., Blechert S. Adv. Synth. Catal. 345:2003;572
27. Connon S.J., Blechert S. Angew. Chem. 115:2003;1944. Angew. Chem., Int. Ed. 2003, 42, 1900
28. Prühs S., Lehmann C.W., Fürstner A. Organometallics. 23:2004;280
29. Yao Q., Zhang Y. J. Am. Chem. Soc. 126:2004;74
30. Hoveyda A.H., Gillingham D.G., Van Veldhuizen J.J., Kataoka O., Garber S.B., Kingsbury J.S., Harrity J.P.A. Org. Biomol. Chem. 2:2004;8
31. For a recent review on molybdenum and tungsten imido alkylidene complexes in olefin methathesis, see: Schrock R.R., Hoveyda A.H. Angew. Chem. 115:2003;4740. Angew. Chem., Int. Ed. 2003, 42, 4592
32. For a short review, see: Perry M.C., Burgess K. Tetrahedron: Asymmetry. 14:2003;951
33. Sheenan J.C., Hunneman D.H. J. Am. Chem. Soc. 88:1966;3666
34. Sheenan J.C., Hara T. J. Org. Chem. 39:1974;1196
35. Enders D., Breuer K., Runsink J. Helv. Chim. Acta. 79:1996;1899
36. Enders D., Breuer K. Helv. Chim. Acta. 79:1996;1217
37. Enders D., Kallfass U. Angew. Chem. 114:2002;1822. Angew. Chem., Int. Ed. 2002, 41, 1743
38. See also: Kerr M.S., Read de Alaniz J., Rovis T. J. Am. Chem. Soc. 124:2002;10298
39. Herrmann W.A., Gooßen L.J., Köcher C., Artus G.R.J. Angew. Chem. 108:1996;2980. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805
40. Enders D., Gielen H., Raabe G., Runsink J., Teles J.H. Chem. Ber. 129:1996;1483
41. Herrmann W.A., Gooßen L.J., Artus G.R.J., Köcher C. Organometallics. 16:1997;2472
42. Enders D., Gielen H., Breuer K. Tetrahedron: Asymmetry. 8:1997;3571
43. Enders D., Gielen H. J. Organomet. Chem. 617-618:2001;70
44. Duan W.-L., Shi M., Rong G.-B. Chem. Commun. 2003;2916
45. Seiders T.J., Ward D.W., Grubbs R.H. Org. Lett. 3:2001;3225
46. Van Veldhuizen J.J., Garber S.B., Kingsbury J.S., Hoveyda A.H. J. Am. Chem. Soc. 124:2002;4954
47. Van Veldhuizen J.J., Gillingham D.G., Garber S.B., Kataoka O., Hoveyda A.H. J. Am. Chem. Soc. 125:2003;12502
48. For reviews about Mo imido alkylidene complexes in asymmetric olefin metathesis see: Hoveyda A.H., Schrock R.R. Chem. Eur. J. 7:2001;945
49. See also Ref. [6r]
50. Guillen F., Winn C.L., Alexakis A. Tetrahedron: Asymmetry. 12:2001;2083
51. Pytkowicz J., Roland S., Mangeney P. Tetrahedron: Asymmetry. 12:2001;2087
52. Alexakis A., Winn C.L., Guillen F., Pytkowicz J., Roland S., Mangeney P. Adv. Synth. Catal. 345:2003;345
53. Lee S., Hartwig J.F. J. Org. Chem. 66:2001;3402
54. Glorius F., Altenhoff G., Goddard R., Lehmann C. Chem. Commun. 2002;2704
55. Bonnet L.G., Douthwaite R.E., Kariuki B.M. Organometallics. 22:2003;4187
56. Ma Y., Song C., Ma C., Sun Z., Chai Q., Andrus M.B. Angew. Chem. 115:2003;6051. Angew. Chem., Int. Ed. 2003, 42, 5871
57. Lee H.M., Smith D.C. Jr., He Z., Stevens E.D., Yi C.S., Nolan S.P. Organometallics. 20:2001;794
58. Lee H.M., Jiang T., Stevens E.D., Nolan S.P. Organometallics. 20:2001;1255
59. Hillier A.C., Lee H.M., Stevens E.D., Nolan S.P. Organometallics. 20:2001;4246
60. For a complex of type 1, where the pyridine is replaced by a phosphine, see: Vázques-Serrano L.D., Owens B.T., Buriak J.M. Chem. Commun. 2002;2518
61. Crabtree R.H., Morris G.E. J. Organomet. Chem. 135:1977;395
62. Crabtree R.H. Acc. Chem. Res. 12:1979;331
63. Albrecht M., Crabtree R.H., Mata J., Peris E. Chem. Commun. 2002;32
64. Albrecht M., Miecznikowski J.R., Samuel A., Faller J.W., Crabtree R.H. Organometallics. 21:2002;3596
65. Powell M.T., Hou D.-R., Perry M.C., Cui X., Burgess K. J. Am. Chem. Soc. 112:2001;8878
66. Perry M.C., Cui X., Powell M.T., Hou D.-R., Reibenspiess J.H., Burgess K. J. Am. Chem. Soc. 125:2003;113
67. Cui X., Burgess K. J. Am. Chem. Soc. 125:2003;14212
68. Seo H., Park H.-J., Kim B.Y., Lee J.H., Son S.U., Chung Y.K. Organometallics. 22:2003;618
69. Seo H., Kim B.Y., Lee J.H., Park H.-J., Son S.U., Chung Y.K. Organometallics. 22:2003;4783
70. Bolm C., Kesselgruber M., Raabe G. Organometallics. 21:2002;707
71. 2-symmetric carbene, see: Broggini D., Togni A. Helv. Chim. Acta. 85:2002;2518
72. Bolm C., Focken T., Raabe G. Tetrahedron:Asymmetry. 14:2003;1733
73. Focken, T. Ph.D. thesis, RWTH Aachen, 2003
74. For a review on the use of [2.2]paracyclophane-based ligands in asymmetric catalysis, see: Gibson S.E., Knight J.C. Org. Biomol. Chem. 1:2003;1256
75. Reich H.J., Cram D.J. J. Am. Chem. Soc. 91:1968;3527
76. Rossen K., Pye P.J., Maliakal A., Volante R.P. J. Org. Chem. 62:1997;6462
77. For other pseudo-ortho-disubstituted [2.2]paracyclophanes (4, 12-disubstituted [2.2]paracyclophanes) having phosphorus-containing substituents, see: Pye P.J., Rossen K., Reamer R.A., Tsou N.N., Volante R.P., Reider P.J. J. Am. Chem. Soc. 119:1997;6207
78. Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997
79. Pye P.J., Rossen K., Reamer R.A., Volante R.P., Reider P.J. Tetrahedron Lett. 39:1998;4441
80. Dyer P.W., Dyson P.J., James S.L., Martin C.M., Suman P. Organometallics. 17:1998;4344
81. Burk M.J., Hems W., Herzberg D., Malan C., Zanotti-Gerosa A. Org. Lett. 2:2000;4173
82. Zanotti-Gerosa A., Malan C., Herzberg D. Org. Lett. 3:2001;3687
83. Rossen K. Angew. Chem. 113:2001;4747. Angew. Chem., Int. Ed. 2001, 40, 4611
84. For the preparation of 1-mesitylimidazole, see: Gardiner M.G., Herrmann W.A., Reisinger C.-P., Schwarz J., Spiegler M. J. Organomet. Chem. 572:1999;239
85. The synthesis of 1-(2, 6-diisopropylphenyl)imidazole was performed analogous to: Howarth J., Al-Hashimy N.A. Tetrahedron Lett. 42:2001;5777
86. For an alternative method, see: Johnson A.L., Kauer J.C., Sharma D.C., Dorfman R.I. J. Med. Chem. 12:1969;1024
87. For a procedure to protect phosphino groups with sulfur and removal of the thio protection group with Ra-Ni, see: Gilbertson S.R., Xie D., Fu Z. J. Org. Chem. 66:2001;7240
88. 6, see: Corey E.J., Chen Z., Tanoury G.J. J. Am. Chem. Soc. 115:1993;11000
89. For the synthesis of sodium tetrakis(3, 5-bis(trifluoromethyl)phenyl) borate (NaBARF), see: Reger D.L., Wright T.D., Little C.A., Lamba J.J.S., Smith M.D. Inorg. Chem. 40:2001;3810
90. Bahr S.R., Boudjouk P. J. Org. Chem. 57:1992;5545
91. Nishida H., Takada N., Yoshimura M. Bull. Chem. Soc. Jpn. 57:1984;2600
92. Brookhart M., Grant B., Volpe A.F. Jr. Organometallics. 11:1992;3920
93. For Ir-catalyzed asymmetric hydrogenation of unfunctionalized alkenes, see: Lightfoot A., Schnider P., Pfaltz A. Angew. Chem. 110:1998;3047. Angew. Chem., Int. Ed. 1998, 37, 2897
94. Hilgraf R., Pfaltz A. Synlett. 1999;1814
95. Blackmond D.G., Lightfoot A., Pfaltz A., Rosner T., Schnider P., Zimmermann N. Chirality. 12:2000;442
96. Blankenstein J., Pfaltz A. Angew. Chem. 113:2001;4577. Angew. Chem., Int. Ed. 2001, 40, 4445
97. Bernardinelli G.H., Kündig E.P., Meier P., Pfaltz A., Radkowski K., Zimmermann N., Neuburger-Zehnder M. Helv. Chim. Acta. 84:2001;3233
98. Cozzi P.G., Zimmermann N., Hilgraf R., Schaffner S., Pfaltz A. Adv. Synth. Catal. 343:2001;450
99. Hou D.-R., Reibenspies J., Colacot T.J., Burgess K. Chem. Eur. J. 7:2001;5391
100. Menges F., Pfaltz A. Adv. Synth. Catal. 344:2002;40
101. Menges F., Neuburger M., Pfaltz A. Org. Lett. 4:2002;4713
102. Tang W., Wang W., Zhang X. Angew. Chem. 115:2003;973. Angew. Chem., Int. Ed. 2003, 42, 943
103. Drury W.J. III, Zimmermann N., Keenan M., Hayashi M., Kaiser S., Goddard R., Pfaltz A. Angew. Chem. 116:2004;72. Angew. Chem., Int. Ed. 2004, 43, 70
104. Schenkel L.B., Ellman J.A. J. Org. Chem. 69:2004;1800
105. Liu D., Tang W., Zhang X. Org. Lett. 6:2004;513
106. For reviews, see: Halterman R.L. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. I:1999;183 Springer, Berlin
107. Pfaltz A., Blankenstein J., Hilgraf R., Hörmann E., McIntyre S., Menges F., Schönleber M., Smidt S.P., Wüstenberg B., Zimmermann N. Adv. Synth. Catal. 345:2003;33
108. Bunlaksananusorn T., Polborn K., Knochel P. Angew. Chem. 115:2003;4071. Angew. Chem., Int. Ed. 2003, 42, 3941
109. Bunlaksananusorn T., Pérez Luna A., Bonin M., Micouin L., Knochel P. Synlett. 2003;2240
110. Xtal3.7 System; Hall, S. R., du Boulay, D. J., Olthof-Hazekamp, R., Eds.; University of Western Australia, 2000
111. Hintermann T., Seebach D. Helv. Chim. Acta. 81:1998;2093
112. Argouarch G., Samuel O., Kagan H.B. Eur. J. Org. Chem. 2000;2885