Mechanism and diastereoselectivity of aziridine formation from sulfur ylides and imines: A computational study

Journal of Organic Chemistry

Volumn 71, Issue 7, 2006, Pages 2726-2734

  Robiette, Raphaël ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE; DFT METHODS; DIASTEREOSELECTIVITY; IMINES; TS STRUCTURES;

COMPUTATION THEORY; CONTINUUM MECHANICS; DESIGN FOR TESTABILITY; HYDROGEN BONDS; SOLVENTS;

SULFUR COMPOUNDS;

AZIRIDINE; BETAINE; IMINE; SOLVENT; SULFUR;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DIELECTRIC CONSTANT; ELIMINATION REACTION; EPOXIDATION; HORNER WADSWORTH EMMONS REACTION; HYDROGEN BOND; REACTION ANALYSIS; RING CLOSING METATHESIS; SOLVENT EFFECT; STEREOCHEMISTRY;

AZIRIDINES; COMPUTER SIMULATION; IMINES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFUR;

EID: 33645517277     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052559t     Document Type: Article

References (60)

1. For reviews, see: (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
2. (b) McCoull, W.; Davis, F. A. Synthesis 2000, 10, 1347-1365.
3. (c) Sweeney, J. Chem. Soc. Rev. 2002, 31, 247-258.
4. (d) Cardillo, G.; Glentilucci, L.; Tolomelli, A. Aldrichimica Acta 2003, 36, 39-50.
5. (e) Lee, W. K.; Ha, H. J. Aldrichimica Acta 2003, 36, 57-65.
6. (e) Yudin, A. K. Aziridines and Epoxides in Synthesis; Wiley-VCH: Weinheim, 2006.
7. For reviews, see: (a) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693-1715.
8. (b) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905-2919.
9. (a) Aggarwal, V. K.; Abdelrahman, H.; Thompson, A.; Mattison, B.; Jones, R. V. H. Phosphorus, Sulfur Silicon 1994, 95, 283-292.
10. (b) Aggarwal, V. K.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Org. Chem. 1996, 61, 8368-8369.
11. (c) Aggarwal, V. K.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. Phosphorus, Sulfur Silicon 1997, 120, 361-362.
12. (d) Aggarwal, V. K.; Alonso, E.; Fang, G. Y.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433-1436.
13. (e) Aggarwal, V. K.; Ferrara, M.; O'Brian, C. J.; Thompson, A.; Jones, R. V. H.; Fieldhouse, R. J. Chem. Soc., Perkin Trans. 1 2001, 14, 1635-1643.
14. (f) Aggarwal, V. K.; Charment, J. P. H.; Ciampi, C.; Hornby, J. M.; O'Brian, C. J.; Hynd, G.; Parsons, R. J. Chem. Soc., Perkin Trans. 1 2001, 1, 3159-3166.
15. (g) Aggarwal, V. K.; Alonso, E.; Ferrara, M.; Spey, S. E. J. Org. Chem. 2002, 67, 2335-2344.
16. (h) Aggarwal, Vasse, J.-L. Org. Lett. 2003, 5, 3987-3990.
17. (a) Li, A.-H.; Dai, L.-X.; Hou, X.-L. Chem. Commun. 1996, 4, 491-492.
18. (b) Li, A.-H.; Dai, L.-X.; Hou, X.-L. J. Chem. Soc., Perkin Trans. 1 1996, 9, 867-869.
19. (c) Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Chen, M.-B. J. Org. Chem. 1996, 61, 4641-4648.
20. (d) Li, A.-H.; Dai, L.-X.; Hou, X.-L. J. Chem. Soc., Perkin Trans. 1 1996, 22, 2725-2729.
21. (e) Li, A.-H.; Dai, L.-X.; Hou, X.-L. J. Chem. Soc., Perkin Trans. 1 1997, 4, 585.
22. (f) Li, A.-H.; Zhou, Y.-G.; Dai, L.-X.; Xia, L.-J.; Lin, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 1317-1319.
23. (g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. J. Chem. Soc., Chem. Commun. 1997, 13, 1231.
24. (h) Zhou, Y.-G.; Li, A.-H.; Hou, X.-L.; Dai, L.-X. Tetrahedron Lett. 1997, 38, 7225-7228.
25. (i) Hou, X.-L.; Yang, X.-F.; Dai, L.-X.; Chen, X.-F. J. Chem. Soc., Chem. Commun. 1998, 7, 747-748.
26. (j) Yang, X.-F.; Zhang, M.-J.; Hou, X.-L.; Dai, L. X. J. Org. Chem. 2002, 67, 8097-8103.
27. For reviews, see: (a) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372.
28. (b) Dai, L.-X.; Hou, X.-L.; Zhou, Y.-G. Pure Appl. Chem. 1999, 71, 369-376.
29. For some other recent studies, see: (a) Saito, T. Sakairi, M.; Akiba, D. Tetrahedron Lett. 2001, 42, 5451-5454.
30. (b) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Synlett 2003, 13, 1985-1988.
31. (c) Solladié-Cavallo, A.; Roje, M.; Welter, R.; Sunjiæ, V. J. Org. Chem. 2004, 69, 1409-1412.
32. (d) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2005, 6, 2377-2380.
33. 2R). The present study will thereby focus only on reactions involving such imines. The nature of the imine group (Ar) has usually little effect on selectivity.
34. (a) Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1-14.
35. (b) Lindvall, M. K.; Koskinen, A. M. P. J. Org. Chem. 1999, 64, 4596-4606.
36. Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5757-5856.
37. Aggarwal, V. K.; Harvey, J. N.; Robiette, R. Angew. Chem., Int. Ed. 2005, 44, 5468-5471.
38. Silva, M. A.; Bellenie, B. R.; Goodman, J. M. Org. Lett. 2004, 6, 2559-2562.
39. It has been shown computationally and experimentally that N-substituted cis aziridines are thermodynamically more stable than the corresponding trans isomers. See: (a) Mimura, N.; Ibuka, T.; Akaji, M.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fijii, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 3, 351-352.
40. (b) Lutz, R. E.; Turner, A. B. J. Org. Chem. 1968, 33, 516-518.
41. (a) Robiette, R.; Richardson, J.; Aggarwal, V. K.; Harvey, J. N. J. Am. Chem. Soc. 2005, 127, 13468-13469.
42. (b) Robiette, R.; Richardson, J.; Aggarwal, V. K.; Harvey, J. N. J. Am. Chem. Soc. 2006, 128, 2394-2409.
43. (a) Brandt, P.; Norrby, P.-O.; Martin, I.; Rein, T. J. Org. Chem. 1998, 63, 1280-1289.
44. (b) Ando, K. J. Org. Chem. 1999, 64, 6815-6821.
45. Jaguar, ver. 4.0; Schrödinger, Inc.: Portland, OR, 1991-2000.
46. Tannor, D. J.; Marten, B.; Murphy, R.; Friesner, R. A.; Sitkoff, D.; Nicholls, A.; Ringnalda, M.; Goddard, W. A., III; Honing, B. J. Am. Chem. Soc. 1994, 116, 11875-11882.
47. Marten, B.; Kim, K.; Cortis, C.; Friesner, R. A.; Murphy, R. B.; Ringnalda, M. N.; Sitkoff, D.; Honing, B. J. Phys. Chem. 1996, 100, 11775-11788.
48. Badoul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys. 1999, 110, 7650-7657.
49. Gaussian 03, Revision B.04; Frisch, M. J. et al.; Gaussian, Inc.: Pittsburgh, 2003.
50. MOLPRO, Version 2002.3; Werner H.-J et al.
51. Even after a careful examination of the TS structures, no CH/π or π/π interactions could be observed in any of them.
52. (a) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449.
53. (b) Grabowski, S. J. J. Phys. Org. Chem. 2004, 17, 18-31.
54. It is recognized that C-H⋯O hydrogen bonding is justified if the fragment under consideration satisfies the following range of parameters: H⋯O distance = 2.0-2.8 Å; C-H⋯O angle = 110-180°; C=O⋯H angle = 120-140° (see ref 21 and references therein). All C-H⋯O hydrogen bonds considered in this study follow this range.
55. a) Robiette, R.; Fang, G. Y.; Harvey, J. N.; Aggarwal, V. K. Chem. Commun. 2006, 741-743.
56. (b) Aggarwal, V. K.; Fuentes, D.; Harvey, J. N.; Hynd, G.; Ohara, D.; Picoul, W.; Robiette, R.; Smith, C.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2006, 128, 2105-2114.
57. N2 reaction (see for instance (a) Bordwell, F. G.; Brannen, W. T. J. Am. Chem. Soc. 1964, 86, 4645-4650.
58. (b) Lee, K. S.; Kumar, K.; Lee, H. W.; Lee, B.-S.; Lee, I. Org. Biomol. Chem. 2003, 1, 1989-1994). We are currently carrying out studies aiming at understanding this dissimilarity.
59. Seeman, J. I. Chem. Rev. 1983, 83, 83-134.
60. The favorable Coulombic interactions present in the cisoid TSs can be expected to be competing with the higher solvation energy for the transoid structures (due to a better access to the polar groups). This difference in solvation energy, while large (for instance, for syn TS in the case of semistabilized ylide, solvation energy is 24.2 and 17.9 kcal/mol for transoid and cisoid TS, respectively), is however not large enough to compensate for the intrinsic lower stability of the transoid structure.