Erratum: Tuning the reactivity of difluoromethyl sulfoximines from electrophilic to nucleophilic: Stereoselective nucleophilic difluoromethylation of aryl ketones (Journal of Medicinal Chemistry (2012) 134:41 (16999-17002) DOI: 10.1021/ja308419a);Tuning the reactivity of difluoromethyl sulfoximines from electrophilic to nucleophilic: Stereoselective nucleophilic difluoromethylation of aryl ketones

Journal of the American Chemical Society

Volumn 134, Issue 41, 2012, Pages 16999-17002

  Shen, Xiao ^a   Zhang, Wei ^a   Ni, Chuanfa ^a   Gu, Yucheng ^b   Hu, Jinbo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS; KETONES; STEREOCHEMISTRY; STEREOSELECTIVITY;

DIASTEREOSELECTIVE ADDITIONS; DIFLUORINATED; NATURAL PRODUCTS; SECONDARY ALCOHOLS; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS; SULFOXIMINES; TERTIARY ALCOHOLS;

TUNING;

KETONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ALKYLATION; ARTICLE; ELECTROPHILICITY; NUCLEOPHILICITY; STEREOCHEMISTRY;

EID: 84867534110     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.9b06390     Document Type: Erratum

References (52)

1. Böhm, H. J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Müller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004, 5, 637
2. Sani, M.; Volonterio, A.; Zanda, M. ChemMedChem 2007, 2, 1693
3. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
4. Fäh, C.; Mathys, R.; Hardegger, L. A.; Meyer, S.; Bur, D.; Diederich, F. Eur. J. Org. Chem. 2010, 4617
5. McCarthy, J. R. Fluorine in Drug Design: A Tutorial Review; 17th Winter Fluorine Conference, St. Pete Beach, FL, 2005.
6. McCarthy, J. R. Utility of Fluorine in Biologically Active Molecules; 219th National Meeting of the American Chemical Society, San Francisco, CA, 2000; Division of Fluorine Chemistry Tutorial.
7. Meanwell, N. A. J. Med. Chem. 2011, 54, 2529
8. Erickson, J. A.; McLoughlin, J. I. J. Org. Chem. 1995, 60, 1626
9. Narjes, F.; Koehler, K. F.; Koch, U.; Gerlach, B.; Colarusso, S.; Steinkühler, C.; Brunetti, M.; Altamura, S.; De Francesco, R.; Matassa, V. G. A. Bioorg. Med. Chem. Lett. 2002, 12, 701
10. Chowdhury, M. A.; Abdellatif, K. R.; Dong, Y.; Das, D.; Suresh, M. R.; Knaus, E. E. J. Med. Chem. 2009, 52, 1525
11. Graneto, M. J.; Philips, W. J.; U.S. Patent 5,093,347, 1992.
12. Gauthier, J. Y. Bioorg. Med. Chem. Lett. 2011, 21, 2836
13. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475
14. Shibata, N.; Mizuta, S.; Kawai, H. Tetrahedron: Asymmetry 2008, 19, 2633
15. Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1
16. Langlois, B. R.; Billard, T. Synthesis 2003, 185
17. Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757
18. Hu, J. J. Fluorine Chem. 2009, 130, 1130
19. Hu, J.; Zhang, W.; Wang, F. Chem. Commun. 2009, 7465
20. Ni, C.; Wang, F.; Hu, J. Beilstein J. Org. Chem. 2008, 4, 21
21. Zhu, L.; Li, Y.; Ni, C.; Hu, J.; Beier, P.; Wang, Y.; Prakash, G. K. S.; Olah, G. A. J. Fluorine Chem. 2007, 128, 1241
22. Bandini, M.; Sinisi, R.; Umani-Ronchi, A. Chem. Commun. 2008, 4360
23. Nie, J.; Zhang, G.-W.; Wang, L.; Fu, A.; Zheng, Y.; Ma, J.-A. Chem. Commun. 2009, 2356
24. Zhang, W.; Ni, C.; Hu, J. Top. Curr. Chem. 2012, 308, 25
25. Ni, C.; Hu, J. Synlett 2011, 770
26. Shen, X.; Zhang, W.; Zhang, L.; Luo, T.; Wan, X.; Gu, Y.; Hu, J. Angew. Chem., Int. Ed. 2012, 51, 6966
27. For the unsuccessful addition of 1 to benzaldehyde, see: Zhang, W. Ph.D. Dissertation, Shanghai Institute of Organic Chemistry, 2010.
28. For the unsuccessful addition of 1 to acetophenone, see the SI.
29. Zhang, W.; Wang, F.; Hu, J. Org. Lett. 2009, 11, 2109
30. Mace, Y.; Magnier, E. Eur. J. Org. Chem. 2012, 2479
31. Nomura, Y.; Tokunaga, E.; Shibata, N. Angew. Chem., Int. Ed. 2011, 50, 1885
32. Prakash, G. K. S.; Zhang, Z.; Wang, F.; Ni, C.; Olah, G. A. J. Fluorine Chem. 2011, 132, 792
33. Urban, C.; Cadoret, F.; Blazejewski, J.-C.; Magnier, E. Eur. J. Org. Chem. 2011, 4862
34. Noritake, S.; Shibata, N.; Nakamura, S.; Toru, T.; Shiro, M. Eur. J. Org. Chem. 2008, 3465
35. Kahraman, M.; Sinishtaj, S.; Dolan, P. M.; Kensler, T. W.; Peleg, S.; Saha, U.; Chuang, S. S.; Bernstein, G.; Korczak, B.; Posner, G. H. J. Med. Chem. 2004, 47, 6854
36. For the effect of different bases on the nucleophilic difluoromethylation with difluoromethyl phenyl sulfone, see: Liu, J.; Hu, J. Chem.-Eur. J. 2010, 16, 11443
37. Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Chem. Soc., Perkin Trans. 1 1994, 2607
38. Ni, C.; Hu, J. Tetrahedron Lett. 2005, 46, 8273
39. Isabel, E. Bioorg. Med. Chem. Lett. 2010, 20, 887
40. Elzen, G. W.; Williams, J.; Vinson, S. B. J. Chem. Ecol. 1984, 10, 1251
41. Weyerstahl, P.; Schneider, S.; Marschall, H.; Rustaiyan, A. Liebigs Ann. Chem. 1993, 111
42. Magiatis, P.; Michaelakis, A.; Skaltsounis, A.-L.; Haroutounian, S. A. Nat. Prod. Lett. 2001, 15, 125
43. Sun, J.; Shi, D.; Ma, M.; Li, S.; Wang, S.; Han, L.; Yang, Y.; Fan, X.; Shi, J.; He, L. J. Nat. Prod. 2005, 68, 915
44. Cakir, A.; Kordali, S.; Kilic, H.; Kaya, E. Biochem. Syst. Ecol. 2005, 33, 245
45. Sylvestre, M.; Pichette, A.; Longtin, A.; Nagau, F.; Legault, J. J. Ethnopharmacol. 2006, 103, 99
46. Kartal, N.; Sokmen, M.; Tepe, B.; Daferera, D.; Polissiou, M.; Sokmen, A. Food Chem. 2007, 100, 584
47. Saroglou, V.; Arfan, M.; Shabir, A.; Hadjipavlou-Litina, D.; Skaltsa, H. Flavour Frag. J. 2007, 22, 154
48. Ho, T.-L.; Liu, S.-H. Synth. Commun. 1983, 13, 463
49. Abecassis, K.; Gibson, S. E. Eur. J. Org. Chem. 2010, 2938
50. Boukpuvalas, J.; Pouliot, R.; Fréchette, Y. Tetrahedron Lett. 1995, 36, 4167
51. Reggelin, M.; Zur, C. Synthesis 2000, 1
52. Organosulfur Chemistry in Asymmetric Synthesis; Toru, T.; Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2008; p 209.