A new family of chiral chelating diamines with transition-metal stereocenters: Synthesis, structure, and reactivity of the enantiomerically pure dirhenium-substituted 1,2-diamine. See abstract

Organometallics

Volumn 20, Issue 14, 2001, Pages 3087-3096

  Alvey, Luke J ^a   Delacroix, Olivier ^b   Wallner, Carsten ^b   Meyer, Oliver ^a   Hampel, Frank ^b   Szafert, Slawomir ^a,c   Lis, Tadeusz ^c   Gladysz, J A ^a,b  

^a UNIVERSITY OF UTAH   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^c UNIVERSITY OF WROC AW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINES; DIRHENIUM; TRANSITION METAL STEREOCENTER;

CHELATION; COMPLEXATION; CRYSTAL STRUCTURE; MIXTURES; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

EID: 0035833284     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010153a     Document Type: Article

References (98)

1. (a) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159.
2. (b) Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580;
3. Angew. Chem. 1998, 110, 2724.
4. Additional lead references from the year 2000: (a) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875.
5. (b) Wiberg, K. B.; Bailey W. F. Tetrahedron Lett. 2000, 41, 9365.
6. Barrett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
7. Additional lead references from the years 1999-2001: (a) Mimoun, H.; de Saint Laumer, J. Y.; Giannini, L.; Scopelliti, R.; Floriani, C. J. Am. Chem. Soc. 1999, 121, 6158.
8. (b) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40;
9. Angew. Chem. 2001, 113, 41.
10. (c) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173.
11. (d) Malkov, A. V.; Spoor, P.; Vinader, V.; Kocovsky, P. Tetrahedron Lett. 2001, 42, 509.
12. (e) Catalysis not requiring a metal: Leclerc, E.; Mangeney, P.; Henryon, V. Tetrahedron: Asymmetry 2000, 11, 3471.
13. (a) Kido, J.; Okamoto, Y.; Brittain, H. G. J. Org. Chem. 1991, 56, 1412.
14. (b) Devitt, P. G.; Mitchell, M. C.; Weetman, J. M.; Taylor, R. J.; Kee, T. P. Tetrahedron: Asymmetry 1995, 6, 2039.
15. (c) Hulst, R.; Koen de Vries, N.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 699.
16. Representative new syntheses from the year 2000: (a) Busacca, C. A.; Campbell, S.; Dong, Y.; Grossbach, D.; Ridges, M.; Smith, L.; Spinelli, E. J. Org. Chem. 2000, 65, 4753.
17. (b) Rivas, F. M.; Riaz, U.; Diver, S. T. Tetrahedron: Asymmetry 2000, 11, 1703.
18. (c) Roland, S.; Mangeney, P. Eur. J. Org. Chem. 2000, 611.
19. (d) Alexakis, A.; Tomassini, A.; Chouillet, C.; Roland, S.; Mangeney, P.; Bernardinelli, G. Angew. Chem., Int. Ed. 2000, 39, 4093.
20. Angew. Chem. 2000, 112, 4259.
21. (e) Yamauchi, T.; Higashiyama, K.; Kubo, H.; Ohmiya, S. Tetrahedron: Asymmetry 2000, 11, 3003.
22. (f) Mitchell, J. M.; Finney, N. S. Tetrahedron Lett. 2000, 41, 8431.
23. (g) Martelli, G.; Morri, S.; Savoia, D. Tetrahedron 2000, 56, 8367.
24. (h) Markidis, T.; Kokotos, G. J. Org. Chem. 2000, 66, 1919.
25. (a) Togni, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1475.
26. Angew. Chem. 1996, 108, 1581.
27. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377.
28. (c) Togni, A.; Bieler, N.; Burckhardt, U.; Köllner, C.; Pioda, G.; Schneider, R.; Schnyder, A. Pure Appl. Chem. 1999, 71, 1531.
29. (a) Spescha, M.; Duffy, N. W.; Robinson, B. H.; Simpson, J. Organometallics 1994, 13, 4895.
30. (b) Crameri, Y.; Foricher, J.; Scalone, M.; Schmid, R. Tetrahedron: Asymmetry 1997, 8, 3617.
31. (c) Woltersdorf, M.; Kranich, R.; Schmalz, H.-G. Tetrahedron 1997, 53, 7219.
32. (d) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950.
33. (e) Schwink, L.; Ireland, T.; Püntener, K.; Knochel, P. Tetrahedron: Asymmetry 1998, 9, 1143.
34. (f) Song, J.-H.; Cho, D.-J.; Jeon, S.-J.; Kim, Y.-H.; Kim, T.-J.; Jeong, J.-H. Inorg. Chem. 1999, 38, 893.
35. (g) Delacroix, O.; Picart-Goetgheluck, S.; Maciejewski, L.; Brocard, J.; Nowogrocki, G. Synlett 2001, 29.
36. (a) Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 10270.
37. (b) Rios, R.; Liang, J.; Lo, M. M.-C.; Fu, G. C. J. Chem. Soc., Chem. Commun. 2000, 377.
38. (c) Related studies with monoamines: Fu, G. C. Acc. Chem. Res. 2000, 33, 412.
39. Brunner, H. Angew. Chem., Int. Ed. 1999, 38, 1194;
40. Angew. Chem. 1999, 111, 1248.
41. (a) Zwick, B. D.; Arif, A. M.; Patton, A. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1987, 26, 910.
42. Angew. Chem. 1987, 99, 921.
43. (b) Kromm, K.; Zwick, B. D.; Meyer, O.; Hampel, F.; Gladysz, J. A. Chem. Eur. J. 2001, 7, 2015.
44. Agbossou, F.; O'Connor, E. J.; Garner, C. M.; Quirós Méndez, N.; Fernández, J. M.; Patton, A. T.; Ramsden, J. A.; Gladysz, J. A. Inorg. Synth. 1992, 29, 211.
45. (a) Dewey, M. A.; Stark, G. A.; Gladysz, J. A. Organometallics 1996, 15, 4798 and references therein.
46. (b) Saura-Llamas, I.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 2136.
47. Dewey, M. A.; Zhou, Y.; Liu, Y.; Gladysz, J. A. Organometallics 1993, 12, 3924.
48. McCormick, F. B.; Gleason, W. B.; Zhao, X.; Heah, P. C.; Gladysz, J. A. Organometallics 1986, 5, 1778.
49. (a) Some of this work is taken from: Alvey, L. J. Ph.D. Thesis, University of Utah, 1999.
50. (b) Wallner, C. Diplom Thesis, University of Erlangen-Nürnberg, 1999.
51. (a) Merrifield, J. H.; Strouse, C. E.; Gladysz, J. A. Organometallics 1982, 1, 1204.
52. (b) Merrifield, J. H.; Lin, G.-Y.; Kiel, W. A.; Gladysz, J. A. J. Am. Chem. Soc. 1983, 105, 5811.
53. Tam, W.; Lin, G.-Y.; Wong, W.-K.; Kiel, W. A.; Wong, V. K.; Gladysz, J. A. J. Am. Chem. Soc. 1982, 104, 141.
54. O'Connor, E. J.; Kobayashi, M.; Floss, H. G.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 109, 4837.
55. 3 Sloan, T. E. Top. Stereochem. 1981, 12, 1.
56. The nonracemic complexes in this study were first synthesized with a rhenium configuration opposite to that used in most previous studies. Although both enantiomers were eventually prepared, all characterization data are from the former series. To facilitate comparisons and analyses, the abstract, Results, and Discussion sections are narrated from the standpoint of the latter (customary) series (including schemes and figures). The compound configurations in the Experimental Section correspond to the work as it was actually conducted. One consequences deserves emphasis: the structures in Figures 1 and 2 are the enantiomers of those crystallographically determined.
57. (a) Braunholtz, J. T.; Ebsworth, E. A. V.; Mann, F. G.; Sheppard, N. J. Chem. Soc. 1958, 2780.
58. (b) Baldwin, D. A.; Leigh, G. J. J. Chem. Soc. A 1968, 1431.
59. (a) Georgiou, S.; Gladysz, J. A. Tetrahedron 1986, 42, 1109.
60. (b) Davies, S. G.; Dordor-Hedgecock, I. M.; Sutton, K. H.; Whittaker, M. J. Am. Chem. Soc. 1987, 109, 5711.
61. Mann, F. G.; Watson, H. R. J. Chem. Soc. 1958, 2772.
62. (a) Abu-Surrah, A. S.; Fawzi, R.; Steimann, M.; Rieger, B. J. Organomet. Chem. 1996, 512, 243.
63. (b) Robinson, D. J.; Kennard, C. H. L. J. Chem. Soc. A 1970, 1008.
64. (c) Haszeldine, R. N.; Young, J. C. Proc. Chem. Soc., London 1959, 394.
65. (d) Iball, J.; MacDougall, M.; Scrimgeour, S. Acta Crystallogr. 1975, B31, 1672.
66. (e) Ito, T.; Marumo, F.; Saito, Y. Acta Crystallogr. 1971, B27, 1695.
67. (f) de Graaf, W.; Boersma, J.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Organometallics 1989, 8, 2907.
68. Lead references to a research team with many relevant papers on group 10-11, 1,2-diamine complexes: (a) De Renzi, A.; Di Blasio, B.; Saporito, A.; Scalone, M.; Vitagliano, A. Inorg. Chem. 1980, 19, 960.
69. (b) Albano, V. G.; Demartin, F.; De Renzi, A.; Morelli, G. Inorg. Chim. Acta 1988, 149, 253.
70. (c) Cucciolito, M. E.; Jama, M. A.; Giordano, F.; Vitagliano, A.; De Felice, V. Organometallics 1995, 14, 1152.
71. (d) Cavallo, L.; Cucciolito, M. E.; De Martino, A.; Giordano, F.; Orabona, I.; Vitagliano, A. Chem. Eur. J. 2000, 6, 1127.
72. (a) Becker, J. J.; White, P. S.; Gagné, M. R. Inorg. Chem. 1999, 38, 798.
73. (b) Zhang, X.; Zhu, Q.; Guzei, I. A.; Jordan, R. F. J. Am. Chem. Soc. 2000, 122, 8093.
74. Bernard, M.; Delbecq, F.; Sautet, P.; Fache, F.; Lemaire, M. Organometallics 2000, 19, 5715.
75. House, D. A. In Comprehensive Coordination Chemistry; Wilkinson, G.; Gillard, R. D.; McCleverty, J. A., Eds.; Pergamon Press, Oxford, U.K. 1987; Vol. 2, p 23.
76. (a) Merrifield, J. H.; Strouse, C. E.; Gladysz, J. A. Organometallics 1982, 1, 1204.
77. (b) Meyer, O.; Arif, A. M.; Gladysz, J. A. Organometallics 1995, 14, 1844.
78. (c) Peng, T.-S.; Arif, A. M.; Gladysz, J. A. J. Chem. Soc., Dalton Trans. 1995, 1857.
79. Otto, M.; Boone, B. J.; Arif, A. M.; Gladysz, J. A. J. Chem. Soc., Dalton Trans. 2001, 1218.
80. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1 (compare the last five entries on page S9 with entries 2-5 page S10).
81. (a) Dewey, M. A.; Knight, D. A.; Klein, D. P.; Arif, A. M.; Gladysz, J. A. Inorg. Chem. 1991, 30, 4995.
82. (b) Amoroso, A. J.; Arif, A. M.; Gladysz, J. A. Organometallics 1997, 16, 6032.
83. Prommesberger, M. Unpublished research reports, University of Erlangen-Nürnberg.
84. Fanizzi, F. P.; Maresca, L.; Natile, G.; Lanfranchi, M.; Manotti-Lanfredi, A. M.; Tiripicchio, A. Inorg. Chem. 1988, 27, 2422.
85. (a) Södergren, M. J.; Andeersson, P. G. J. Am. Chem. Soc. 1998, 120, 10760 and reviews cited therein.
86. (b) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2567;
87. Angew. Chem. 1996, 108, 2726.
88. Alvey, L. J.; Meier, R.; Soós, T.; Bernatis, P.; Gladysz, J. A. Eur. J. Inorg. Chem. 2000, 1975.
89. Buhro, W. E.; Georgiou, S.; Fernández, J. M.; Patton, A. T.; Strouse, C. E.; Gladysz, J. A. Organometallics 1986, 5, 956.
90. Anderson, G. K.; Lin, M. Inorg. Synth. 1990, 28, 60.
91. These assignments were made based upon chemical shifts predicted by ChemNMR-Pro (Cambridge Software).
92. Sheldrick, G. M. SHELX-76; University of Cambridge, Cambridge, U.K., 1976.
93. (a) Sheldrick, G. M. SHELX-93, Program for Refinement of Crystal Structures; University of Göttingen, Göttingen, Germany, 1993.
94. (b) Sheldrick, G. M. SHELXL-93. In Crystallographic Computing 3; Sheldrick, G. M., Krüger C., Goddard, R., Eds.; Oxford University Press: Oxford, U.K., 1993; pp 175-189.
95. Flack, H. D. Acta Crystallogr, 1981, A37, 734. Limiting values are 0 for the correct structure and +1 for the inverted structure.
96. (a) "Collect" Data Collection Software; Nonius BV, 1998.
97. (b) Otwinowski, Z.; Minor, W. "Scalepack" Data Processing Software. In Methods Enzymol. 1997, 276 (Macromolecular Crystallography, Part A), 307.
98. Cromer, D. T.; Waber, J. T. In International Tables for X-ray Crystallography; Ibers, J. A., Hamilton, W. C., Eds.; Kynoch: Birmingham, England, 1974.