Stereoselective coupling of prochiral radicals with a chiral C2-symmetric nitroxide

Journal of the American Chemical Society

Volumn 122, Issue 35, 2000, Pages 8421-8434

  Braslau, Rebecca ^a   Naik, Neeta ^a   Zipse, Hendrik ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

NITROXIDE; RADICAL; SOLVENT;

ARTICLE; CALCULATION; CHEMICAL REACTION KINETICS; CHIRALITY; DIELECTRIC CONSTANT; ELECTRON SPIN RESONANCE; HYDROPHILICITY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STEREOSPECIFICITY; TEMPERATURE; VISCOSITY;

EID: 0033832739     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000520u     Document Type: Article

References (92)

1. (a) Curran, D. P. Synthesis 1988, 417-439.
2. (b) Curran, D. P. Synthesis 1988, 489-513.
3. (c) Curran, D. P. Chem. Rev. 1991, 91, 1237-1286.
4. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: New York. 1996.
5. Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163-171.
6. (a) Nanni, D.; Curran, D. P. Tetrahedron: Asymmetry 1996, 7, 2417-2422.
7. (b) Blumenstein, M.; Schwarzkopf, K.; Metzger, J. O. Angew. Chem., Int. Ed. Engl. 1997, 36, 235-236.
8. (c) Schwarzkopf, K.; Blumenstein, M.; Hayen, A.: Metzger, J. O. Eur. J. Org. Chem. 1998, 177, 7-181.
9. (d) Haque, M. B.; Roberts, B. P. Tetrahedron Lett. 1996, 37, 9123-9126.
10. (e) Haque, M. B.; Roberts, B. P.; Tocher, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 2881-2889.
11. (f) Dakternieks, D.; Dunn, K.; Perchyonok, V. T.; Schiesser, C. H. J. Chem. Soc., Chem. Commun. 1999, 1665-1666.
12. (g) A tin hydride bearing (L)-borneol prepared in situ: Schumann, H.; Pachaly, B.; Schuetze, B. C. J. Organomet. Chem. 1984, 265, 145-152.
13. (a) Fukuzawa, S.; Seki, K.; Tatsuzawa, M.; Mutoh, K. J. Am. Chem. Soc. 1997, 119, 1482-1483.
14. (b) Sibi, M. Personal communication.
15. Mikami, K.; Yamaoka, M. Tetrahedron Lett. 1998, 39, 4501-4504.
16. (a) For a discussion of diastereoselective radical-radical self-dimerizations and stereoselectivity in geminate radical pair recombinations, see: ref 2, pp 242-250.
17. (b) Enantiomeric recoginition in radical recombination has been studied in the context of the 1,2-Wittig rearrangement: Tomooka, K.; Igarashi, T.; Nakai, T. Tetrahedron Lett. 1993, 34, 8139-8142.
18. For a discussion of persistent radicals reacting with transient radicals, see: Fischer, H. J. Am. Chem. Soc. 1986, 108, 3925-3927.
19. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1976, 8, 13-19.
20. (a) Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992-4996.
21. (b) Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1988, 53, 1629-1632.
22. (c) Arends, I. W. C. E.; Mulder, P.; Clark, K. B.; Wayner, D. D. M. J. Phys. Chem. 1995, 99, 8182-8189.
23. (a) Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Ang. Chem., Int. Ed. Eng. 1997, 36, 237-238.
24. (b) Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron: Asymmetry 1997, 8, 3209-3212.
25. Stereoselective coupling of acyclic chiral nitroxides with prochiral radicals will be reported separately. Braslau, R.; Chaplinski, V. Manuscript in preparation.
26. (a) Puts, R. S.; Sogah D. Y. Macromolecules 1996, 29, 3323-3325.
27. (b) Benfaremo, N.; Steenbock, M.; Klapper, M.; Müllen, K.; Enkelmann, V.; Cabrera, K. Liebigs Ann. Chem. 1996, 1413-1415.
28. (c) Einhorn, J.; Einhorn. C.; Ratajczak, F.; Gautier-Luneau, I.; Pierre, J.-L. J. Org. Chem. 1997, 62, 9385-9388.
29. Kornblum, N.; Wade, P. A. J. Org. Chem. 1973, 38, 1418-1420.
30. Braslau, R.; Burrill, L. C.; Siano, M.; Naik, N.; Howden, R. K.; Mahal, L. K. Macromolecules 1997, 30, 6445-6450.
31. Dao, J.; Benoit, D.; Hawker, C. J. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 2161-2167.
32. (a) Falck, J. R.; Mekonnen, B.; Yu, J. R.; Lai, J. Y. J. Am. Chem. Soc. 1996, 118, 6096-6097.
33. (b) You, S.; Neuenschwander, M. Chimia 1992, 46, 377-380.
34. (a) Poupart, M.-A.; Lassalle, G.; Paquette, L. A. Org. Synth. 1990, 69, 173-179.
35. (b) Ramig, K.; Kuzemko, M. A.; McNamara, K.; Cohen, T. J. Org. Chem. 1992, 57, 1968-1969.
36. (c) Schwartz, E. B.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1992, 114, 10775-10784.
37. Jahn, U. J. Org. Chem. 1998, 63, 7130-7131.
38. (a) Porter, N. A.; Rosenstein, I. J. Tetrahedron Lett. 1993, 34, 7865-7868.
39. (b) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457-4460.
40. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p 695.
41. For a study on the effect of steric bulk on the rate of nitroxides coupling with carbon radicals, see: Iwao, K.; Sakakibara, K.; Hirota, M. J. Comput. Chem. 1998, 19, 215-221.
42. (a) Finney, N. S.; Pospisil, P. J.; Chang, S.; Palucki, M.; Konsler, R. G.; Hansen, K. B.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 1997, 36, 1720-1723 and references therein.
43. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214.
44. Palucki, M.; Finney, N. S.; Pospisil, P. J.; Guler, M. L.; Ishida, T.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 948-954.
45. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure; Wiley: New York, 1992; p 280.
46. Linde, C.; Åermark, B.; Norrby, P.-O.; Svensson, M. J. Am. Chem. Soc. 1999, 121, 5083-5084.
47. (a) Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 491-494.
48. (b) Corey, E. J.; Gross, A. W. J. Org. Chem. 1985, 50, 5391-5393.
49. Myers, A. G.; Movassaghi, M. J. Am. Chem. Soc. 1998, 120, 8891-8892.
50. Schmidt, S. P.; Brooks, D. W. Tetrahedron Lett. 1987, 28, 767-768.
51. Keoshkerian, B.; Georges, M.; Quinlan, M.; Veregin, R.; Goodbrand, B. Macromolecules 1998, 31, 7559-7561.
52. Guindon, Y.; Liu, Z. P.; Jung, G. J. Am. Chem. Soc. 1997, 119, 9289-9290.
53. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857-9864.
54. The variable temperature ESR spectra can be obtained from the Supporting Information.
55. The ESR spectra at -78 °C and -38 °C can be obtained from the Supporting Information.
56. Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983-4992.
57. Valgimigli, L.; Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 9966-9971.
58. Ciriano, M. V.; Korth, H.-G.; van Scheppingen, W. B.; Mulder, P. J. Am. Chem. Soc. 1999, 121, 6375-6381.
59. All values were obtained from the Handbook of Chemistry and Physics, 56th ed.; CRC Press: Boca Raton, FL, 1975; pp E-56-E-57, except for THF: Carvajal, C.; Tolle, K. J.; Smid, J.; Szwarc, M. J. Am. Chem. Soc. 1965, 87, 5548-5553.
60. All values were obtained from the Handbook of Chemistry and Physics, 56th ed.; CRC Press: Boca Raton, FL, 1975; pp E-56-E-57, except for THF: Carvajal, C.; Tolle, K. J.; Smid, J.; Szwarc, M. J. Am. Chem. Soc. 1965, 87, 5548-5553.
61. 2O and toluene: Handbook of Chemistry and Physics, 56th ed.; CRC Press: Boca Raton, FL, 1975; pp F-52-F-55.
62. (b) t-BuOH: Viswanth, D. S.; Natarajan, G. Data Book on the Viscosity of Liquids; Hemisphere Pub. Corp.: New York, 1989.
63. (c) THF: Carvajal, C.; Tolle, K. J.; Smid, J.; Szwarc, M. J. Am. Chem. Soc. 1965, 87, 5548-5553.
64. Fischer, H.; Paul, H. Acc. Chem. Res. 1987, 20, 200-206.
65. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1988, 53, 1629-1632.
66. (a) Kothe, T.; Marque, S.; Martschke, R.; Popov, M.; Fischer, H. J. Chem. Soc., Perkin Trans. 2 1998, 1553-1559.
67. (b) Fischer, H. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 1885-1901.
68. Skene, W. G.; Belt, S. T.; Connolly, J. J.; Hahn, P.; Scaiano, J. C. Macromolecules 1998, 31, 9103-9105.
69. 13C NMR spectra illustrating this dynamic behavior, see the Supporting Information.
70. (a) Anderson, J. E.; Corrie, J. E. T. J. Chem. Soc., Perkin Trans. 2 1992, 1027-1031.
71. (b) Anderson, J. E.; Casarini, D.; Corrie, J. E. T.; Lunazzi, L. J. Chem. Soc., Perkin Trans. 2 1993, 1299-1304.
72. (c) Brown, T. M.; Cooksey, C. J.; Crich, D.; Dronsfield, A. T.; Ellis, R. J. Chem. Soc., Perkin Trans. 1 1993, 2131-2136.
73. (a) Busfield, W. K.; Jenkins, I. A.; Thang, S. H.; Moad, G.; Rizzardo, E.; Solomon, D. H. J. Chem. Soc., Chem. Commun. 1985, 1249-1250.
74. (b) Beckwith, A. L. J.; Bowry, V. W.; Moad, G. J. Org. Chem. 1988, 53, 1632-1641.
75. Moad, G.; Rizzardo, E. Macromolecules 1995, 28, 8722-8728.
76. Eliel, E. L.; Wilen S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994; p 877.
77. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
78. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
79. (c) Hertwig, R. H.; Koch, W. J. Comput. Chem. 1995, 16, 576-585.
80. Schaefer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577.
81. All calculations have been performed with Gaussian 98, Revision A.7, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1998.
82. Marsal, P.; Roche, M.; Tordo, P.; de Sainte Claire, P. D. J. Phys. Chem. A 1999, 103, 2899-2905.
83. (a) Dunning, T. H. Jr. J. Chem. Phys. 1989, 90, 1007-1023.
84. (b) Kendall, R. A.; Dunning, T. H. Jr.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6769-6806.
85. (c) Davidson, E. R. Chem. Phys. Lett. 1996, 220, 514-518.
86. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560-571.
87. Chen, W.; Schlegel, H. B. J. Chem. Phys. 1994, 101, 5957-5968.
88. This choice is motivated by the CCSD(T) results which indicate that the onset of C-O bond formation is located at around 2.3 Å. The onset for bond formation in larger model systems occurs at slightly shorter bond distances as compared to the minimal system at the BLYP level of theory.
89. (a) Dunitz, J. D.; Lehn, J. M.; Wipf, G. J. Am. Chem. Soc. 1974, 96, 1956-1957.
90. (b) Bürgi, H. B.; Dunitz, J. D.; Lehn, J. M.; Wipf, G. Tetrahedron 1974, 30, 1563-1572.
91. (a) Bürgi, H. B.; Dunitz, J. D.; Shefter, E. J. Am. Chem. Soc. 1973, 95, 5065-5067.
92. (b) Bürgi, H. B.; Dunitz, J. D. Acc. Chem. Res. 1983, 16, 153-161.