Enantioselective nitrene transfer to sulfides catalyzed by a chiral iron complex

Angewandte Chemie - International Edition

Volumn 52, Issue 33, 2013, Pages 8661-8665

  Wang, Jun ^a   Frings, Marcus ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

asymmetric catalysis; iron; sulfides; sulfimides; sulfoximines

Indexed keywords

ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; IRON COMPLEX; NITRENES; SULFIDES; SULFIMIDES; SULFOXIMINES;

CATALYSIS; ENANTIOSELECTIVITY; IRON; SULFUR COMPOUNDS;

IRON COMPOUNDS;

EID: 84882414485     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201304451     Document Type: Article

References (72)

1. T. L. Gilchrist, C. J. Moody, Chem. Rev. 1977, 77, 409
2. N. Furukawa, S. Oae, Ind. Eng. Chem. Prod. Res. Dev. 1981, 20, 260
3. I. V. Koval, Sulfur Rep. 1993, 14, 149
4. P. C. Taylor, Sulfur Rep. 1999, 21, 241.
5. S. Raghavan, S. R. Reddy, K. A. Tony, C. N. Kumar, S. Nanda, Synlett 2001, 851
6. J. P. Marino, N. Zou, Org. Lett. 2005, 7, 1915
7. A. Padwa, S. Nara, Q. Wang, J. Org. Chem. 2005, 70, 8538
8. Q. Wang, S. Nara, A. Padwa, Org. Lett. 2005, 7, 839
9. A. Padwa, S. Nara, Q. Wang, Tetrahedron Lett. 2006, 47, 595
10. S. Raghavan, C. N. Kumar, Tetrahedron Lett. 2006, 47, 1585
11. M. Candy, C. Guyon, S. Mersmann, J.-R. Chen, C. Bolm, Angew. Chem. 2012, 124, 4516
12. Angew. Chem. Int. Ed. 2012, 51, 4440
13. G. P. Silveira, J. P. Marino, J. Org. Chem. 2013, 78, 3379.
14. H. Takada, M. Oda, A. Oyamada, K. Ohe, S. Uemura, Chirality 2000, 12, 299
15. V. V. Thakur, N. S. C. R. Kumar, A. Sudalai, Tetrahedron Lett. 2004, 45, 2915.
16. R. Vanacore, A.-J. L. Ham, M. Voehler, C. R. Sanders, T. P. Conrads, T. D. Veenstra, K. B. Sharpless, P. E. Dawson, B. G. Hudson, Science 2009, 325, 1230.
17. T. Bach, C. Körber, Tetrahedron Lett. 1998, 39, 5015
18. T. Bach, C. Körber, Eur. J. Org. Chem. 1999, 1033
19. W. Ou, Z.-C. Chen, Synth. Commun. 1999, 29, 4443
20. A. L. Marzinzik, K. B. Sharpless, J. Org. Chem. 2001, 66, 594
21. H. Okamura, C. Bolm, Org. Lett. 2004, 6, 1305
22. G. Y. Cho, C. Bolm, Org. Lett. 2005, 7, 4983
23. G. Y. Cho, C. Bolm, Tetrahedron Lett. 2005, 46, 8007
24. O. García Mancheño, C. Bolm, Org. Lett. 2006, 8, 2349
25. O. García Mancheño, C. Bolm, Chem. Eur. J. 2007, 13, 6674
26. O. García Mancheño, J. Dallimore, A. Plant, C. Bolm, Org. Lett. 2009, 11, 2429
27. O. García Mancheño, J. Dallimore, A. Plant, C. Bolm, Adv. Synth. Catal. 2010, 352, 309
28. A. Pandey, C. Bolm, Synthesis 2010, 2922.
29. G. Celentano, S. Colonna, Chem. Commun. 1998, 701
30. H. Takada, K. Ohe, S. Uemura, Angew. Chem. 1999, 111, 1367
31. Angew. Chem. Int. Ed. 1999, 38, 1288.
32. G. Guanti, C. Dell'Erba, G. Gaiani, Phosphorus Sulfur Relat. Elem. 1976, 1, 179
33. R. Annunziata, M. Cinquini, S. Colonna, F. Cozzi, J. Chem. Soc. Perkin Trans. 1 1981, 3118
34. C. Dell'Erba, M. Novi, G. Garbarino, G. P. Corallo, Tetrahedron Lett. 1983, 24, 1191
35. C. S. Tomooka, E. M. Carreira, Helv. Chim. Acta 2002, 85, 3773
36. F. Collet, R. H. Dodd, P. Dauban, Org. Lett. 2008, 10, 5473.
37. H. Takada, Y. Nishibayashi, K. Ohe, S. Uemura, Chem. Commun. 1996, 931
38. H. Takada, Y. Nishibayashi, K. Ohe, S. Uemura, C. P. Baird, T. J. Sparey, P. C. Taylor, J. Org. Chem. 1997, 62, 6512
39. Y. Miyake, H. Takada, K. Ohe, S. Uemura, J. Chem. Soc. Perkin Trans. 1 1998, 2373.
40. H. Nishikori, C. Ohta, E. Oberlin, R. Irie, T. Katsuki, Tetrahedron 1999, 55, 13937
41. H. Nishikori, T. Katsuki, Appl. Catal. A 2000, 194-195, 475
42. C. Ohta, T. Katsuki, Tetrahedron Lett. 2001, 42, 3885.
43. M. Murakami, T. Uchida, T. Katsuki, Tetrahedron Lett. 2001, 42, 7071
44. M. Murakami, T. Katsuki, Tetrahedron Lett. 2002, 43, 3947
45. M. Murakami, T. Uchida, B. Saito, T. Katsuki, Chirality 2003, 15, 116
46. T. Uchida, Y. Tamura, M. Ohba, T. Katsuki, Tetrahedron Lett. 2003, 44, 7965
47. Y. Tamura, T. Uchida, T. Katsuki, Tetrahedron Lett. 2003, 44, 3301.
48. H. Fujita, T. Uchida, R. Irie, T. Katsuki, Chem. Lett. 2007, 36, 1092.
49. C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217
50. A. Correa, O. García Mancheño, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108
51. E. B. Bauer, Curr. Org. Chem. 2008, 12, 1341
52. C. Bolm, Nat. Chem. 2009, 1, 420
53. R. H. Morris, Chem. Soc. Rev. 2009, 38, 2282
54. K. Junge, K. Schröder, M. Beller, Chem. Commun. 2011, 47, 4849
55. M. Darwish, M. Wills, Catal. Sci. Technol. 2012, 2, 243
56. K. Gopalaiah, Chem. Rev. 2013, 113, 3248.
57. M. Redlich, M. M. Hossain, Tetrahedron Lett. 2004, 45, 8987 (additions of diazo compounds to imines)
58. M. Nakanishi, A.-F. Salit, C. Bolm, Adv. Synth. Catal. 2008, 350, 1835 (additions of PhIï£NTs to olefins).
59. 13C NMR spectra recorded at 25°C.
60. D. J. Cram, J. Day, D. R. Rayner, D. M. von Schriltz, D. J. Duchamp, D. C. Garwood, J. Am. Chem. Soc. 1970, 92, 7369.
61. For the synthesis of racemic sulfoximines using this approach, see:, D. Craig, S. J. Gore, M. I. Lansdell, S. E. Lewis, A. V. W. Mayweg, A. J. P. White, Chem. Commun. 2010, 46, 4991.
62. For a recent overview on sulfoximine chemistry, see:, C. Worch, A. C. Mayer, C. Bolm, in Organosulfur Chemistry in Asymmetric Synthesis (Eds.:, T. Toru, C. Bolm,), Wiley-VCH, Weinheim, 2008, pp. 209 -229.
63. S. J. Park, H. Buschmann, C. Bolm, Bioorg. Med. Chem. Lett. 2011, 21, 4888
64. X. Y. Chen, H. Buschmann, C. Bolm, Synlett 2012, 2808
65. S. J. Park, H. Baars, S. Mersmann, H. Buschmann, J. M. Baron, P. M. Amann, K. Czaja, H. Hollert, K. Bluhm, R. Redelstein, C. Bolm, ChemMedChem 2013, 8, 217.
66. Sulfide 1 ah was prepared according to the reported procedure:, R. Desmond, U. Dolling, B. Marcune, R. Tillyer, D. Tschaen, (Merck and Co., Inc.), US005585504A, 1996.
67. Y. Tamura, S. M. Bayomi, K. Sumoto, M. Ikeda, Synthesis 1977, 693
68. C. P. Baird, P. C. Taylor, J. Chem. Soc. Chem. Commun. 1995, 893
69. C. P. Baird, P. C. Taylor, J. Chem. Soc. Perkin Trans. 1 1998, 3399.
70. A. C. Mayer, A.-F. Salit, C. Bolm, Chem. Commun. 2008, 5975; for related theoretical studies, see
71. Y. Moreau, H. Chen, E. Derat, H. Hirao, C. Bolm, S. Shaik, J. Phys. Chem. B 2007, 111, 10288.
72. The enantiospecificity was calculated according to the following equation: es [%]=(enantiomeric excess of epoxide 6 m /enantiomeric excess of sulfimide 2 m)×100 %. For the first use of this term, see:, S. E. Denmark, T. Vogler, Chem. Eur. J. 2009, 15, 11737.