2-(p-Tolylsulfinyl)benzyl halides as efficient precursors of optically pure trans-2,3-Disubstituted aziridines

Chemistry - A European Journal

Volumn 16, Issue 32, 2010, Pages 9874-9883

  Arroyo, Yolanda ^a   Meana, Ángela ^a   Sanz Tejedor, M Ascensión ^a   Alonso, Inés ^b   García Ruano, José Luis ^b  

^a UNIVERSITY OF VALLADOLID   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Asymmetric synthesis; Aziridination; Chiral aziridines; Diastereoselectivity; Sulfinylimines

Indexed keywords

ASYMMETRIC SYNTHESIS; AZIRIDINATION; CHIRAL AZIRIDINES; DIASTEREO-SELECTIVITY; SULFINYLIMINES;

SODIUM; STEREOSELECTIVITY;

ORGANIC COMPOUNDS;

EID: 77955873698     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000217     Document Type: Article

References (98)

1. For reviews, see: a) M. Braun, Angew. Chem. 1998, 110, 444-465;
2. Angew. Chem. Int. Ed. 1998, 37, 430-451;
3. b) G. Boche, C.W. Lohrenz, Chem. Rev. 2001, 101, 697-756;
4. c) A. Basu, S. Thayumanavan, Angew. Chem. 2002, 114, 740-763;
5. Angew. Chem. Int. Ed. 2002, 41, 716-738;
6. d) M. Braun in The Chemistry of Organolithium Compounds (Eds.: Z. Rappoport, I. Marek), Wiley, New York, 2004, Chapter 13, pp. 829-898.
7. For leading and recent references, see : a) H. C. Stiasny, R. W. Hoffmann, Chem. Eur. J. 1995, 1, 619- 624;
8. b) R. W. Hoffmann, H.-C. Stiasny, J. Krüger, Tetrahedron 1996, 52, 7421-7434;
9. c) M. Shimizu, T. Hata, T. Hiyama, Heterocycles 2000, 52, 707-717;
10. d) M. Shimizu, T. Fujimoto, X. Y. Liu, H. Minezaki, T. Hata, T. Hiyama, Tetrahedron 2003, 59, 9811-9823;
11. e) P. R. Blakemore, S. P. Marsden, H. D. Vater, Org. Lett. 2006, 8, 113-116;
12. f) B. A. Pearlman, S. R. Putt, X A. Fleming, J. Org. Chem. 2006, 71, 5646-5677.
13. For a review, see : A. De Meijere, M. Vonseebach, S. Zollner, S. I. Kozhushkov, V. N. Belov, R. Boese, T. Haumann, J. Benetbuchholz, D. S. Yufit, J. A. K. Howard, Chem. Eur. J. 2001, 7, 4021-4034, and references therein.
14. For recent references, see: a) J. Kvícala, A. Pelter, Collect. Czech. Chem. Commun. 2001, 66, 1508-1520;
15. b) H. Yanagisawa, K. Miura, M. Kitamura, K. Narasaka, K. Ando, Helv. Chim. Acta 2002, 85, 3130-3135;
16. c) H. Yanagisawa, K. Miura, M. Kitamura, K. Narasaka, K. Ando, Bull. Soc. Chim. 2003, 76, 2009-2026;
17. d) Y.H. Li, L. Lu, X. M. Zhao, Org. Lett. 2004, 6, 4467-4470;
18. e) M. Braun, A. Hohmann, J Rahematpura, C. Buhne, S. Grimme, Chem. Eur. J. 2004, 10, 4584-4593.
19. For recent references, see: a) G. J. Gordon, T. Luker, M. W. Tuckett, R. J Whitby, Tetrahedron 2000, 56, 2113-2129;
20. b) S. Dixon, S. M. Fillery, A. Kasatkin, D.T.E. Norton, R. J. Whitby, Tetrahedron 2004, 60, 1401-1416.
21. For recent references, see: a) H. Hermann, J. C. W. Lohrenz, A. Kuhn, G. Boche, Tetrahedron 2000, 56, 4109-4115;
22. b) J. Kvicala, J. Stambasky, S. Bohm, O. Paleta, J. Fluorine Chem. 2002, 113, 147-154;
23. c) L. M. Pratt, B. Ramachandran, J.D. Xidos, C.J. Cramer, D. G. Truhlar, J. Org. Chem. 2002, 67, 7607-7612;
24. d) L. M. Pratt, N. Van Nguyen, L. T. Le, J. Org. Chem. 2005, 70, 2294-2298;
25. e) L. M. Pratt, L.T. Le, T. N. Truong, J. Org. Chem. 2005, 70, 8298-8302;
26. f) F. M. Bickelhaupt, H. L. Hermann, G. Boche, Angew. Chem. 2006, 118, 838-841;
27. Angew. Chem. Int. Ed. 2006, 45, 823-826;
28. g) K. Ando, J. Org. Chem. 2006, 71, 1837-1850.
29. G. L. Closs, R. A. Moss, J. Am. Chem. Soc. 1964, 86, 4042-4053.
30. R. A. Olofson, C.M. Dougherty, J. Am. Chem. Soc. 1973, 95, 581-582.
31. H. Andringa, Y. A. Heus-Kloos, L. Brandsma, J. Organomet. Chem. 1987, 336, C41-C43.
32. a) S. Florio, L. Troisi, J. Org. Chem. 1996, 61, 4148-4150;
33. b) V. Capriati, S. Florio, R. Luisi, Synlett 2005, 1359-1369;
34. c) V. Capriati, S. Florio, F. M. Perna, Chem. Eur. J. 2009, 15, 7958-7979.
35. a) J. L. García Ruano, M. C. Carreño, M. A. Toledo, J. M. Aguirre, M. T. Aranda, J. Fischer, Angew. Chem. 2000, 112, 2848-2849;
36. Angew. Chem. Int. Ed. 2000, 39, 2736-2737;
37. b) J. L. García Ruano, J. Alemán, J.F. Soriano, Org. Lett. 2003, 5, 677-680;
38. c) J. L. García Ruano, M. T. Aranda, J. M. Aguirre, Tetrahedron 2004, 60, 5383-5392;
39. d) J. L. García Ruano, J. Alemán, J. A. Parra, J. Am. Chem. Soc. 2005, 127, 13048-13054;
40. e) J. L. García Ruano, J. Aleman, B. Cid, Synthesis 2006, 687-686;
41. f) J. L. Garcia Ruano, V. Marcos, J. Alemán, Angew. Chem. 2008, 120, 6942-6945;
42. Angew. Chem. Int. Ed. 2008, 47, 6836-6839;
43. g) J. L. García Ruano, J. Alemán, S. Catalán, V. Marcos, S. Monteagudo, A. Parra, C. Pozo, S. Fustero, Angew. Chem. 2008, 120, 8059-8062;
44. Angew. Chem. Int. Ed. 2008, 47, 7941-7944;
45. h) J. L. García Ruano, A. Parra, V. Marcos, C. del. Pozo, S. Catalán, S. Monteagudo, S. Fustero, J. Am. Chem. Soc. 2009, 131, 9432-9441;
46. i) J. L. García Ruano, V. Marcos, J. Alemán, Synthesis 2009, 3339-3349.
47. J. L. García Ruano, J. Alemán, Org. Lett. 2003, 5, 4513-4516.
48. a) Y. Arroyo, A. Meana, J. F. Rodríguez, M. Santos, M. A. Sanz-Tejedor, J. L. García Ruano, J. Org. Chem. 2005, 70, 3914-3920;
49. b) Y. Arroyo, A. Meana, J. F. Rodríguez, M. Santos, M. A. Sanz-Tejedor, J. L. García Ruano, J. Org. Chem. 2007, 72, 1035-1038;
50. c) Y. Arroyo, A. Meana, J. F. Rodríguez, M. A. Sanz-Tejedor, I. Alonso, J. L. García Ruano, J. Org. Chem. 2009, 74, 764-772.
51. J. L. García Ruano J. Alemán, I. Alonso, A. Parra, V. Marcos, J. Aguirre, Chem. Eur. J. 2007, 13, 6179-6195.
52. a) S. R. Rajski, R. M. Williams, Chem. Rev. 1.998, 98, 2723-2796;
53. b) T. J. Hodgkinson, T. J. M. Shipman, Tetrahedron 2001, 57, 4467-4488;
54. c) S. Fürmeier, J. O. Metzger, Eur. J. Org. Chem. 2003, 649-659.
55. For reviews on this subject, see: a) D. Tanner, Angew. Chem. 1994, 106, 625-646;
56. Angew. Chem. Int. Ed. Engl. 1994, 33, 599-619;
57. b) H. M. I. Osborn, J. Sweeney, Tetrahedron: Asymmetry 1997, 8, 1693-1715;
58. c) A-H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341-2372;
59. d) T. Ibuka, Chem. Soc. Rev. 1998, 27, 145-154;
60. e) W. McCoull, F. A. Davis, Synthesis 2000, 1347-1365;
61. f) J. B. Sweeney, Chem. Soc. Rev. 2002, 31, 247-258;
62. g) P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905-2919;
63. h) X. E. Hu, Tetrahedron 2004, 60, 2701-2743;
64. i) X. L. Hou, J. Wu, R. H. Fan, C. H. Ding, Z. B. Luo, X. L. Dai, Synlett 2006, 181-193.
65. J. L. García Ruano, J. Alemán, A. Parra, A. Alcudia, C. Maya, J. Org. Chem. 2009, 74, 2145-2152.
66. Y. Arroyo, A. Meana, M. A. Sanz-Tejedor, J. L. Garcia Ruano, Org. Lett. 2008, 10, 2151-2154.
67. J. L. García Ruano, J. Alemán, A. Padwa, Org. Lett. 2004, 6, 1757-1760.
68. F. K. Davis, R. E. Reddy, J. M. Szewczyk, G. V. Reddy, P. S. Portonovo, H. Zhang, D. Fanelli, R. T. Reddy, P. Zhou, P. J. Carrol, J. Org. Chem. 1997, 62, 2555-2563.
69. J. A. Ellman, D. A. Cogan, T. P. Tang, G. Liu, T. D. Owens, J. Org. Chem. 1999, 64, 1278-1284.
70. The eliminative dimerization of lithium carbenoids to give alkenes has been extensively studied. In these processes, the 1, 2-elimination of LiBr is very fast, see: a) B. J. Wakefield in Organolithium Methods, Academic Press, London, 1988;
71. b) V. Capriati, S. Florio, R. Luisi, M. T. Rochetti, J. Org. Chem. 2002, 67, 759-763; see also reference [1d].
72. M. Julia, J. N. Verpaux, T. Zahneisen, Synlett 1990, 769-770.
73. It is noteworthy that reactions of N-fert-butylsulfinylimines derived from aromatic aldehydes with (S)-3 afforded complex mixtures of compounds the complete analysis of which was not possible in our hands.
74. CCDC-719589 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif. See also the Supporting Information.
75. Recent reviews: a) Z. Zhijun, I. D. G. Watson, A. K. Yudin, J. Am. Chem. Soc. 2005, 127, 17516-17529;
76. b) I. D. G. Watson, A. K. Yudin, Acc. Chem. Res. 2006, 39, 194-206. Others references, see:
77. c) L. Gentilucci, Y. Grijzen, L. Thijs, B. Zwanenburg, Tetrahedron Lett. 1995, 36, 4665-4668;
78. d) F. A. Davis, Y. Zhang, A. Rao, Z. Zhang, Tetrahedron 2001, 57, 6345-6352;
79. e) F. A. Davis, J. Deng, Y. Zhang, R. C. Haltiwanger, Tetrahedron 2002, 58, 7135-7143;
80. f) F. A. Davis, Y. Wu, H. Yan, W. McCoull, K. R. Prasad, J. Org. Chem. 2003, 68, 2410-2419.
81. Y. Arroyo, A. Meana, J. F. Rodriguez, M. Santos, M. A. Sanz-Tejedor, J. L. García Ruano, Tetrahedron 2006, 62, 8525-8532.
82. Y. Arroyo, A. Meana, J. F. Rodríguez, M. A. Sanz-Tejedor, I. Alonso, J. L. García Ruano, J. Org. Chem. 2009, 74, 4217-4224.
83. a) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
84. b) A. D. Becke, J. Chem. Phys. 1993, 98, 1372-1377.
85. Gaussian 03, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K.N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
86. Geometries have been fully optimized by using the standard 631G(d) basis set for all the atoms except I: a) R. Ditchfield, W.J. Hehre, J. A. Pople, J. Chem. Phys. 1971, 54, 724-728;
87. b) M. M. Francl, W. J. Petro, W. J. Hehre, J. S. Binkley M. S. Gordon, D. J. DeFrees, J. A. Pople, J. Chem. Phys. 1982, 77, 3654-3665; the LANL2DZ basis set supplemented with an ad function of exponent 0.289 was used for iodine;
88. c) P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299-310;
89. d) A. Höllwarth, M. Böhme, S. Dapprich, A. W. Ehlers, A. Gobbi, V. Jonas, K. F. Köhler, R. Stegmann, A. Veldkamp, G. Frenking, Chem. Phys. Lett. 1993, 208, 237-240; frequencies and zero-point energy (ZPE) were also computed at the same level of theory. Final energies have been obtained by using the more extended 6-311,+ G** basis set for all atoms except iodine:
90. e) A. D. McLean, G. S. Chandler, J. Chem. Phys. 1980, 72, 5639-5648;
91. f) R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650-654; For I, a basis set of similar quality (SDB-aug-ccpVTZ) was used:
92. -1) were evaluated at the B3LYP/6-311 + G** level with ZPE and entropy corrections evaluated at 298 K by using the frequencies previously calculated at the B3LYP/6-31G(d) level. Because of the importance of solvent effects, especially when charged species are involved, model structures I-V have also been optimized in a dielectric medium mimicking THF, by using the IEF-PCM model:
93. h) E. Cancès, B. Mennucci, J. J. Tomasi, J. Chem. Phys. 1997, 107, 3032-3041;
94. i) M. Cossi, V. Barone, B. Mennucci, J. Tomasi, Chem. Phys. Lett. 1998, 286, 253-260; in the case of model transition states, this optimization including solvent effects was not possible.
95. Complexes of type I and II, varying the N-Li-C-I dihedral angle, and type III, varying the C-S-O-Li dihedral angle, turned out to be less stable (see the Supporting Information for complexes Ib, IIb and IIIb).
96. This imine was used as a model in our previous study of the reaction of dimethylsulfonium derivatives (see reference [28]). The rotamer with the sulfinyl oxygen atom in a (s)-cis arrangement with respect to the C=N bond was the most stable. However, solvent effects and stabilizing interactions within the transition states can dramatically modify the conformation around the N-S bond.
97. -1) predicts a trans/cis ratio of 97:3, much higher than the 72:28 ratio experimentally observed with alkyl imines (Table 2, entry 10).
98. B. B. Lohray, J. R. Ahujas, J. Chem. Soc. Chem. Commun. 1991, 95-97.