Sulfoxide-to-sulfilimine conversions: Use of modified Burgess-type reagents

Advanced Synthesis and Catalysis

Volumn 355, Issue 17, 2013, Pages 3363-3368

  Hendriks, Christine M M ^a   Lamers, Philip ^a   Engel, Julien ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Burgess reagent; sulfilimines; sulfoxides; sulfoximines; synthetic methods

Indexed keywords

EID: 84888292211     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300766     Document Type: Article

References (70)

1. C. R. Johnson, Acc. Chem. Res. 1973, 6, 341-347
2. M. Reggelin, C. Zur, Synthesis 2000, 1-64
3. 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
4. R. Bentley, Chem. Soc. Rev. 2005, 34, 609-624
5. H.-J. Gais, Heteroat. Chem. 2007, 18, 472-481.
6. M. Harmata, Chemtracts 2003, 16, 660-666
7. H. Okamura, C. Bolm, Chem. Lett. 2004, 33, 482-487
8. C. Bolm, in: Asymmetric Synthesis with Chemical and Biological Methods, (Eds.:, D. Enders, K.-E. Jaeger,), Wiley-VCH, Weinheim, 2007, pp 149-176
9. C. Bolm, Latv. J. Chem. 2012, 49-50.
10. H. R. Bentley, E. E. McDermott, J. K. Whitehead, Nature 1950, 165, 735
11. H. R. Bentley, E. E. McDermott, J. Pace, J. K. Whitehead, T. Moran, Nature 1950, 165, 150-151
12. H. R. Bentley, E. E. McDermott, J. Pace, J. K. Whitehead, T. Moran, Nature 1949, 163, 675-676.
13. Y. Zhu, M. R. Loso, G. B. Watson, T. C. Sparks, R. B. Rogers, J. X. Huang, B. C. Gerwick, J. M. Babcock, D. Kelley, V. B. Hegde, B. M. Nugent, J. M. Renga, I. Denholm, K. Gorman, G. J. DeBoer, J. Hasler, T. Meade, J. D. Thomas, J. Agric. Food Chem. 2011, 59, 2950-2957
14. J. M. Babcock, C. B. Gerwick, J. X. Huang, M. R. Loso, G. Nakamura, S. P. Nolting, R. B. Rogers, T. C. Sparks, J. Thomas, G. B. Watson, Y. Zhu, Pest. Manag. Sci. 2011, 67, 328-334
15. G. B. Watson, M. R. Loso, J. M. Babcock, J. M. Hasler, T. J. Letherer, C. D. Young, Y. Zhu, J. E. Casida, T. C. Sparks, Insect. Biochem. Mol. Biol. 2011, 41, 432-439
16. T. C. Sparks, M. R. Loso, G. B. Watson, J. M. Babcock, V. J. Kramer, Y. Zhu, B. M. Nugent, J. D. Thomas, in: Modern Crop Protection Compounds, 2 nd edn., Vol. 3, (Eds.:, W. Kraemer, U. Schirmer, P. Jeschke, M. Witschel,), Wiley-VCH, Weinheim, 2012, pp 1226-1237.
17. U. Lücking, R. Jautelat, M. Krueger, T. Brumby, P. Lienau, M. Schaefer, H. Briem, J. Schulze, A. Hillisch, A. Reichel, A. M. Wengner, G. Siemeister, ChemMedChem 2013, 8, 1067-1085
18. G. Siemeister, U. Lücking, A. M. Wengner, P. Lienau, W. Steinke, C. Schatz, D. Mumberg, K. Ziegelbauer, Mol. Cancer Ther. 2012, 11, 2265-2273
19. J. Krueger, J. Gries, K. Lovis, J. Hassfeld, WO Patent WO-A1 038411, 2012.
20. For a recent overview on the use of sulfoximines in medicinal chemistry, see:, U. Lücking, Angew. Chem. 2013, 125, 9570-9580
21. Angew. Chem. Int. Ed. 2013, 52, 9399-9408.
22. 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, 217-220
23. X. Y. Chen, S. J. Park, H. Buschmann, M. De Rosa, C. Bolm, Bioorg. Med. Chem. Lett. 2012, 22, 4307-4309
24. X. Y. Chen, H. Buschmann, C. Bolm, Synlett 2012, 23, 2808-2810
25. S. J. Park, H. Buschmann, C. Bolm, Bioorg. Med. Chem. Lett. 2011, 21, 4888-4890.
26. J. K. Whitehead, H. R. Bentley, J. Chem. Soc. 1952, 1572-1574
27. R. Fusco, F. Tericoni, Chim. Ind. (Milan) 1965, 47, 61-62
28. C. R. Johnson, M. Haake, C. W. Schrock, J. Am. Chem. Soc. 1970, 92, 6594-6598
29. R. H. Rynbrandt, D. P. Balgoyen, J. Org. Chem. 1978, 43, 1824-1825
30. for a recent industrial application of this method (on a 0.034 mol scale) in the synthesis of a factor Xa inhibitor, see:, V. Pandya, M. Jain, G. Chakrabarti, H. Soni, B. Parmar, B. Chaugule, J. Patel, T. Jarag, J. Joshi, N. Joshi, A. Rath, V. Unadkat, B. Sharma, H. Ajani, J. Kumar, K. V. V. M. Sairam, H. Patel, P. Patel, Eur. J. Med. Chem. 2012, 58, 136-152.
31. Y. Tamura, K. Sumoto, J. Minamikawa, M. Ikeda, Tetrahedron Lett. 1972, 4137-4140
32. C. R. Johnson, R. A. Kirchoff, H. G. Corkins, J. Org. Chem. 1974, 39, 2458-2459
33. for studies on the stability of MSH, see:, J. Mendiola, J. A. Rincõn, C. Mateos, J. F. Soriano, Ó. de Frutos, J. K. Niemeier, E. M. Davis, Org. Process Res. Dev. 2009, 13, 263-267.
34. For a comparative study of metal-catalyzed iminations and deprotection protocols, see:, O. García Mancheño, C. Bolm, Chem. Eur. J. 2007, 13, 6674-6681
35. for an alternative electrochemical method, see:, T. Siu, A. K. Yudin, Org. Lett. 2002, 4, 1839-1842.
36. O. García Mancheño, O. Bistri, C. Bolm, Org. Lett. 2007, 9, 3809-3811
37. O. García Mancheño, C. Bolm, Org. Lett. 2007, 9, 2951-2954
38. A. Pandey, C. Bolm, Synthesis 2010, 2922-2925.
39. N-Cyanosulfoximines such as Sulfoxaflor (1) can also be prepared by cyanations of NH-sulfoximines with cyanogen bromide (BrCN). For a recent industrial application of this method, see:, C. Gnamm, A. Jeanguenat, A. C. Dutton, C. Grimm, D. P. Kloer, A. J. Crossthwaite, Bioorg. Med. Chem. Lett. 2012, 22, 3800-3806. For analogous cyanation reactions with sulfondiimines, see
40. R. Appel, G. Vollmer, Chem. Ber. 1970, 103, 2555-2561
41. M. Candy, C. Guyon, S. Mersmann, J.-R. Chen, C. Bolm, Angew. Chem. 2012, 124, 4516-4519
42. Angew. Chem. Int. Ed. 2012, 51, 4440-4443.
43. S. Raghavan, S. Mustafa, K. Rathore, Tetrahedron Lett. 2008, 49, 4256-4259.
44. G. M. Atkins, E. M. Burgess, J. Am. Chem. Soc. 1968, 90, 4744-4745
45. E. M. Burgess, H. R. Penton, E. A. Taylor, J. Am. Chem. Soc. 1970, 92, 5224-5226.
46. S. Santra, Synlett 2009, 328-329
47. S. Khapli, S. Dey, D. Mal, J. Indian Inst. Sci. 2001, 81, 461-476
48. C. Lamberth, J. Prakt. Chem. 2000, 342, 518-522.
49. Y. Macé, C. Urban, C. Pradet, J. Marrot, J.-C. Blazejewski, E. Magnier, Eur. J. Org. Chem. 2009, 3150-3153
50. C. Urban, Y. Macé, F. Cadoret, J.-C. Blazejewski, E. Magnier, Adv. Synth. Catal. 2010, 352, 2805-2814.
51. L. Jäger, B. Freude, R. Skirl, K. Schubert, H. Köhler, Z. anorg. allg. Chem. 1993, 619, 711-717.
52. N-Methylpiperidine was chosen based on observations reported in:, T. A. Metcalf, R. Simionescu, T. Hudlicky, J. Org. Chem. 2010, 75, 3447-3450. Use of quinuclidine afforded a very stable, but unreactive reagent.
53. CCDC 943120 (2b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
54. For preparation of sulfoxides, see the Supporting Information and, J. M. Shreeve, J.-J. Yang, R. L. Kirchmeier, U.S. Patent 6,215,021 (B1), 2001.
55. D. Wodka, M. Robbins, P. Lan, R. L. Martinez, J. Athanasopoulos, G. M. Makara, Tetrahedron Lett. 2006, 47, 1825-1828
56. C. T. Brain, J. M. Paul, Y. Loong, P. J. Oakley, Tetrahedron Lett. 1999, 40, 3275-3278
57. T. C. Brain, J. M. Paul, Synlett 1999, 1642-1644.
58. M. Frings, D. Goedert, C. Bolm, Chem. Commun. 2010, 46, 5497-5499
59. H. S. Veale, J. Levin, D. Swern, Tetrahedron Lett. 1978, 503-506.
60. O. García Mancheño, J. Dallimore, A. Plant, C. Bolm, Adv. Synth. Catal. 2010, 352, 309-316.
61. For initial studies on acidic N-deprotections of sulfoximines, see:, P. Stoss, G. Satzinger, Tetrahedron Lett. 1973, 267-268.
62. B. Rodríguez, T. Rantanen, A. Bruckmann, C. Bolm, Adv. Synth. Catal. 2007, 349, 2213-2233
63. A. Stolle, T. Szuppa, S. E. S. Leonhardt, B. Ondruschka, Chem. Soc. Rev. 2011, 40, 2317-2329
64. P. Chauhan, S. S. Chimni, Beilstein J. Org. Chem. 2012, 8, 2132-2141
65. S. L. James, C. J. Adams, C. Bolm, D. Braga, P. Collier, T. Friscic, F. Grepioni, K. D. M. Harris, G. Hyett, W. Jones, A. Krebs, J. Mack, L. Maini, A. G. Orpen, I. P. Parkin, W. C. Shearouse, J. W. Steed, D. C. Waddell, Chem. Soc. Rev. 2012, 41, 413-447.
66. C. R. Johnson, J. J. Rigau, J. Org. Chem. 1968, 33, 4340-4343
67. B. W. Christensen, A. Kjaer, J. Chem. Soc. D 1969, 934-935
68. B. W. Christensen, J. Chem. Soc. D 1971, 597-598
69. D. C. Garwood, M. R. Jones, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 1925-1936, and references cited therein.
70. Prepared according to:, S. H. Zhao, O. Samuel, H. B. Kagan, Org. Synth. Coll. Vol. 1993, 8, 464; 1990, 68, 49- 55.