Solvent and TMEDA effects on the configurational stability of chiral lithiated aryloxiranes

Chemistry - A European Journal

Volumn 17, Issue 29, 2011, Pages 8216-8225

  Perna, Filippo Maria ^a   Salomone, Antonio ^a   Dammacco, Mariangela ^a   Florio, Saverio ^a   Capriati, Vito ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

configurational stability; epoxides; kinetics; ligand effects; lithiation; solvent effects

Indexed keywords

CONFIGURATIONAL STABILITY; EPOXIDES; LIGAND EFFECTS; LITHIATION; SOLVENT EFFECTS;

CHELATION; SOLVENTS; STYRENE;

ORGANIC SOLVENTS;

EPOXIDE; ETHYLENEDIAMINE DERIVATIVE; LITHIUM DERIVATIVE; N,N,N',N' TETRAMETHYLETHYLENEDIAMINE; N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE; SOLVENT; STYRENE OXIDE;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM;

EPOXY COMPOUNDS; ETHYLENEDIAMINES; LITHIUM COMPOUNDS; MOLECULAR CONFORMATION; SOLVENTS; STEREOISOMERISM;

EID: 79959948228     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100351     Document Type: Article

References (89)

1. For reviews, see: a) G. Boche, J. C. W. Lohrenz, Chem. Rev. 2001, 101, 697-756
2. M. Braun, Angew. Chem. 1998, 110, 444-465
3. Angew. Chem. Int. Ed. 1998, 37, 430-451
4. M. Braun, in The Chemistry of Organolithium Compounds, Vol.2 (Eds.:, Z. Rappoport, I. Marek,), Wiley, New York, 2004, Chapter 13
5. V. Capriati, S. Florio, Chem. Eur. J. 2010, 16, 4152-4162; see also
6. P. R. Blakemore, M. S. Burge, J. Am. Chem. Soc. 2007, 129, 3068-3069
7. J. L. Stymiest, V. Bagutski, R. M. French, V. K. Aggarwal, Nature 2008, 456, 778-782
8. V. Bagutski, R. M. French, V. K. Aggarwal, Angew. Chem. 2010, 122, 5268-5271
9. Angew. Chem. Int. Ed. 2010, 49, 5142-5145.
10. The dichotomous reactivity of lithiated styrene oxide has been recently investigated by NMR and DFT calculations:, V. Capriati, S. Florio, F. M. Perna, A. Salomone, A. Abbotto, M. Amedjkouh, S. O. Nilsson Lill, Chem. Eur. J. 2009, 15, 7958-7979.
11. R. E. Gawley, in Topics in Stereochemistry, Vol. 26: Stereochemical Aspects of Organolithium Compounds (Eds.:, R. E. Gawley, J. Siegel,), Wiley-VCH, Weinheim, 2010, Chapter 3.
12. J. Clayden, Tetrahedron Organic Chemistry Series, Vol 26: Organolithiums: Selectivity for Synthesis (Eds.:, J. E. Baldwin, R. M. Williams,) Pergamon, Amsterdam, 2002
13. P. Beak, T. A. Johnson, D. D. Kim, S. H. Lim, in Topics in Organometallic Chemistry, Vol. 5: Organolithiums in Enantioselective Synthesis (Ed.:, D. M. Hodgson,), Springer, Heidelberg, 2003, pp. 139-176
14. D. Hoppe, F. Marr, M. Brügemann, in Topics in Organometallic Chemistry, Vol. 5: Organolithiums in Enantioselective Synthesis (Ed.:, D. M. Hodgson,), Springer, Heidelberg, 2003, pp. 61-137
15. G. Wu, M. Huang, Chem. Rev. 2006, 106, 2596-2616.
16. For leading references tackling the relationship between configurational stability and aggregation, see: a) H. J. Reich, M. A. Medina, M. D. Bowe, J. Am. Chem. Soc. 1992, 114, 11003-11004
17. P. I. Arvidsson, P. Ahlberg, G. Hilmersson, Chem. Eur. J. 1999, 5, 1348-1354
18. F. Haeffner, P. Brandt, R. E. Gawley, Org. Lett. 2002, 4, 2101-2104
19. P. Brandt, F. Haeffner, J. Am. Chem. Soc. 2003, 125, 48-49
20. V. Capriati, S. Florio, R. Luisi, F. M. Perna, A. Spina, J. Org. Chem. 2008, 73, 9552-9564.
21. H. Ott, C. Däschlein, D. Leusser, D. Schildbach, T. Seibel, D. Stalke, C. Strohmann, J. Am. Chem. Soc. 2008, 130, 11901-11911
22. H. Ott, U. Pieper, D. Leusser, U. Flierler, J. Henn, D. Stalke, Angew. Chem. 2009, 121, 3022-3026
23. Angew. Chem. Int. Ed. 2009, 48, 2978-2982
24. V. H. Gessner, C. Däschlein, C. Strohmann, Chem. Eur. J. 2009, 15, 3320-3334.
25. For leading reviews on the reactivity of oxiranyllithiums, see: a)F. Chemla, E. Vranken, in The Chemistry of Organolithium Compounds, Vol. 2 (Eds.:, Z. Rappoport, I. Marek,), John Wiley & Sons, New York, 2004, pp. 1165-1242
26. D. M. Hodgson, C. D. Bray, in Aziridines and Epoxides in Organic Synthesis (Ed.:, A. K. Yudin,), Wiley-VCH, Weinheim, 2006, pp. 145-184
27. V. Capriati, S. Florio, R. Luisi, Chem. Rev. 2008, 108, 1918-1942.
28. V. Capriati, S. Florio, A. Salomone, in Topics in Stereochemistry, Vol. 26: Stereochemical Aspects of Organolithium Compounds (Eds.:, R. E. Gawley, J. S. Siegel,), Wiley-VCH, Weinheim, 2010, Chapter 4.
29. A. Basu, S. Thayumanavan, Angew. Chem. 2002, 114, 740-763
30. Angew. Chem. Int. Ed. 2002, 41, 716-738
31. P. Monje, M. R. Paleo, L. García-Río, F. J. Sardina, J. Org. Chem. 2008, 73, 7394-7397
32. D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410
33. Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316.
34. V. Capriati, S. Florio, R. Luisi, A. Salomone, M. G. Tocco, A. M. Martín Castro, J. L. García Ruano, E. Torrente, Tetrahedron 2009, 65, 383-388.
35. V. Capriati, S. Florio, F. M. Perna, A. Salomone, Chem. Eur. J. 2010, 16, 9778-9788.
36. S. T. Kerrick, P. Beak, J. Am. Chem. Soc. 1991, 113, 9708-9710
37. W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622-2636
38. R. E. Gawley, Q. Zhang, Tetrahedron 1994, 50, 6077-6088
39. A. Carstens, D. Hoppe, Tetrahedron 1994, 50, 6097-6108
40. N. J. Ashweek, P. Brandt, I. Coldham, S. Dufour, R. E. Gawley, F. Haeffner, R. Klein, G. Sanchez-Jimenez, J. Am. Chem. Soc. 2005, 127, 449-457
41. T. I. Yousaf, R. L. Williams, I. Coldham, R. E. Gawley, Chem. Commun. 2008, 97-98
42. R. E. Gawley, Q. Zhang, J. Am. Chem. Soc. 1993, 115, 7515-7516
43. H. Ahlbrecht, J. Harbach, R. W. Hoffmann, T. Ruhland, Liebigs Ann. 1995, 211-216; for recent papers dealing with the influence of Lewis bases on organolithium structure and reactivity, see
44. C. Strohmann, V. H. Gessner, A. Damme, Chem. Commun. 2008, 3381-3383
45. C. Strohmann, V. H. Gessner, J. Am. Chem. Soc. 2007, 129, 8952-8953.
46. For some leading reviews discussing the carbanion dynamics of chiral organolithiums, see: a) ref. [3] b) I. Coldham, N. S. Sheikh, in Topics in Stereochemistry, Vol. 26: Stereochemical Aspects of Organolithium Compounds, (Eds.:, R. E. Gawley, J. S. Siegel,), Wiley-VCH, Weinheim, 2010, Chapter 7.
47. TMEDA has also been proven to play a crucial role in other types of reactions. For example, a recent paper by Nagashima and co-workers suggests a leading role of TMEDA in iron-catalyzed cross-coupling reactions of ArMgX with alkyl halides:, D. Noda, Y. Sunada, T. Hatakeyama, N. Nakamura, H. Nagashima, J. Am. Chem. Soc. 2009, 131, 6078-6079.
48. enant)]:, H. Eyring, Chem. Rev. 1935, 17, 65-77.
49. D. B. Collum, Acc. Chem. Res. 1992, 25, 448-454.
50. D. Stern, N. Finkelmeier, K. Meindl, J. Henn, D. Stalke, Angew. Chem. 2010, 122, 7021-7024
51. Angew. Chem. Int. Ed. 2010, 49, 6869-6872
52. D. Stern, N. Finkelmeier, D. Stalke, Chem. Commun. 2011, 47, 2113-2115.
53. Interestingly, in the case of N-Boc-2-lithiopiperidine (Boc=tert-butoxycarbonyl), the rate of enantiomerization with varying amounts of TMEDA revealed a first-order dependence on [TMEDA] instead:, I. Coldham, D. Leonori, T. K. Beng, R. E. Gawley, Chem. Commun. 2009, 5239-5241.
54. G. Fraenkel, M. Henrichs, M. Hewitt, B. M. Su, J. Am. Chem. Soc. 1984, 106, 255-256
55. D. R. Hay, Z. Song, S. G. Smith, P. Beak, J. Am. Chem. Soc. 1988, 110, 8145-8153
56. 14]hexane at 183 K. Such an upfield shift is consistent with an increase in the negative charge on the carbanion due to complexation of the lithium by the above diamine, see also:, J. M. Catala, G. Clouet, J. Brossas, J. Organomet. Chem. 1981, 219, 139-143
57. McKeever et al. have also demonstrated that tetrameric methyllithium maintains its association in TMEDA:, L. D. McKeever, R. Waak, M. A. Doran, E. B. Baker, J. Am. Chem. Soc. 1969, 91, 1057-1061.
58. M. C. Whisler, S. MacNeil, V. Snieckus, P. Beak, Angew. Chem. 2004, 116, 2256-2276
59. Angew. Chem. Int. Ed. 2004, 43, 2206-2225; for other papers dealing with the intermediacy of substrate-organolithium complexes, see
60. A. I. Meyers, L. M. Fuentes, W. F. Reiker, J. Am. Chem. Soc. 1983, 105, 2082-2083
61. J. J. Fitt, H. W. Gschwend, J. Org. Chem. 1984, 49, 209-210
62. I. Fernández, J. González, F. López-Ortiz, J. Am. Chem. Soc. 2004, 126, 12551-12564
63. D. Stead, G. Carbone, P. O'Brian, K. R. Campos, I. Coldham, A. Sanderson, J. Am. Chem. Soc. 2010, 132, 7260-7261.
64. F. Marr, R. Fröhlich, D. Hoppe, Org. Lett. 1999, 1, 2081-2083.
65. A multinuclear magnetic resonance investigation recently carried out on (S,S)-trans-α-lithiated diphenylaziridine in toluene has shown, for example, that it exists as a configurationally stable homochiral TMEDA-solvated dimer:, V. Capriati, S. Florio, R. Luisi, A. Mazzanti, B. Musio, J. Org. Chem. 2008, 73, 3197-3204.
66. For papers dealing with Cl-Li coordination, see: a) A. Abbotto, S. Bradamante, S. Florio, V. Capriati, J. Org. Chem. 1997, 62, 8937-8940
67. S. Florio, V. Capriati, R. Luisi, A. Abbotto, D. J. Pippel, Tetrahedron 2001, 57, 6775-6786.
68. Hammett θ constants have been taken from the following review:, C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.
69. V. Capriati, M. Dammacco, S. Florio, F. M. Perna, A. Salomone, Phosphorus, Sulfur Silicon Relat. Elem. 2010, DOI:.
70. F. G. Bordwell, G. D. Cooper, J. Am. Chem. Soc. 1952, 74, 1058-1060
71. H. H. Szmant, G. Suld, J. Am. Chem. Soc. 1956, 78, 3400-3403
72. C. Y. Meyers, Gazz. Chim. Ital. 1963, 93, 1206-1221
73. F. G. Bordwell, G. J. McCollum, J. Org. Chem. 1976, 41, 2391-2395
74. F. G. Bordwell, J. E. Bares, J. E. Bartmess, G. E. Drucker, J. Gerhold, G. J. McCollum, M. Van Der Puy, N. R. Vanier, W. S. Matthews, J. Org. Chem. 1977, 42, 326-332
75. M. Charton, in Progress in Physical Organic Chemistry, Vol. 13: Electrical Effect Substituent Constants for Correlation Analysis (Ed.:, R. W. Taft,), Wiley, New York, 1981, 119-251
76. theory also predicts that the attachment of electron-withdrawing groups to sulfur contracts sulfur d orbitals, thereby enhancing their bonding properties, see:, D. P. Craig, E. A. Magnusson, J. Chem. Soc. 1956, 4895-4908.
77. V. Wehner, P. Braun, B. Sachse, (Hoechst AG, Frankfurt, DE), Substituted β-hydroxyethylamine fungicides, DE 4210569, 1993.
78. A. Nagaki, E. Takizawa, J. Yoshida, Chem. Eur. J. 2010, 16, 14149-14158.
79. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519.
80. E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1965, 87, 1353-1364.
81. E. Akguen, M. B. Glinski, K. L. Dhawan, T. Durst, J. Org. Chem. 1981, 46, 2730-2734.
82. S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315.
83. T. Hamada, T. Torii, K. Izawa, T. Ibariya, Tetrahedron 2004, 60, 7411-7417.
84. N. Ikemoto, J. Liu, K. M. J. Brands, J. M. McNamara, P. J. Reider, Tetrahedron 2003, 59, 1317-1325.
85. J. Deregnaucourt, A. Archelas, F. Barbirato, J.-M. Paris, R. Furstoss, Adv. Synth. Catal. 2007, 349, 1405-1417.
86. S. A. Weissman, K. Rossen, P. J. Reider, Org. Lett. 2001, 3, 2513-2515
87. Org. Lett. 2005, 7, 2803.
88. R. Zhang, W.-Y. Yu, H.-Z. Sun, W.-S. Liu, C.-M. Che, Chem. Eur. J. 2002, 8, 2495-2507.
89. K. Matsumoto, T. Kubo, T. Katsuki, Chem. Eur. J. 2009, 15, 6573-6575.