Enantioselective synthesis of cyclopropanes that contain fluorinated tertiary stereogenic carbon centers: A chiral α-fluoro carbanion strategy

Angewandte Chemie - International Edition

Volumn 51, Issue 28, 2012, Pages 6966-6970

  Shen, Xiao ^a   Zhang, Wei ^a   Zhang, Lei ^a   Luo, Tao ^a   Wan, Xiaolong ^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

asymmetric synthesis; chiral fluoroalkylation reagent; cyclopropanation; fluorine; sulfoximine

Indexed keywords

ASYMMETRIC SYNTHESIS; CHIRAL FLUOROALKYLATION REAGENT; CYCLOPROPANATION; DIASTEREO-SELECTIVITY; ENANTIOSELECTIVE SYNTHESIS; STEREOGENIC CARBONS; SULFOXIMINES;

CARBON; ENANTIOSELECTIVITY; FLUORINE;

PROPANE;

ANION; CARBON; CYCLOPROPANE DERIVATIVE; FLUORINATED HYDROCARBON;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; HALOGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANIONS; CARBON; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOPROPANES; HALOGENATION; HYDROCARBONS, FLUORINATED; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 84863678904     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201202451     Document Type: Article

References (58)

1. "Biochemistry of the Cyclopropyl Group": H. W. Liu, C. T. Walsh, in The Chemistry of the Cyclopropyl Group (Ed.:, Z. Rappoport,), Wiley, New York, 1987, p. 959
2. J. Salaün, Top. Curr. Chem. 2000, 207, 1.
3. H. J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, M. Stahl, ChemBioChem 2004, 5, 637
4. M. Sani, A. Volonterio, M. Zanda, ChemMedChem 2007, 2, 1693
5. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320
6. C. Fäh, R. Mathys, L. A. Hardegger, S. Meyer, D. Bur, F. Diederich, Eur. J. Org. Chem. 2010, 2010, 4617.
7. J. R. McCarthy, Fluorine in Drug Design: A Tutorial Review, 17th Winter Fluorine Conference (St. Pete Beach, FL, USA), 2005
8. J. R. McCarthy, Utility of Fluorine in Biologically Active Molecules, 219th National Meeting of the American Chemical Society (San Francisco, CA, USA), 2000.
9. D. Seyferth, R. A. Woodruff, J. Org. Chem. 1973, 38, 4031
10. O. Tamura, M. Hashimoto, Y. Kobayashi, T. Katoh, K. Nakatani, M. Kamada, I. Hayakawa, T. Akiba, S. Terashima, Tetrahedron Lett. 1992, 33, 3483
11. M. Kamada, I. Hayakawa, T. Akiba, A. Terajima, O. Tamura, J. Kobayashi, M. Hashimoto, T. Katoh, K. Nakatani, Japanese Patent 04327568, 1992
12. W. M. P. Johnson, G. Holan, K. E. Tarvis, Aust. J. Chem. 1986, 39, 271
13. A. Toyota, Y. Ono, C. Kaneko, I. Hayakawa, Tetrahedron Lett. 1996, 37, 8507
14. O. G. J. Meyer, R. Frohlich, G. Haufe, Synthesis 2000, 2010, 1479
15. W. P. Dailey, Tetrahedron Lett. 1987, 28, 5801.
16. S. Hruschka, R. Fröhlich, P. Kirsch, G. Haufe, Eur. J. Org. Chem. 2007, 141.
17. V. Gouverneur, O. Lozano in, Science of Synthesis: Stereoselective Synthesis Vol.3 (Ed.: J. G. de Vries, G. A. Molander, P. A. Evans), Thieme, Stuttgart, 2011, p. 851
18. L. L. Cao, L. B. Gao, S. T. Ma, Z. P. Liu, Curr. Org. Chem. 2010, 14, 889
19. D. Cahard, X. H. Xu, S. Couve Bonnaire, X. Pannecoucke, Chem. Soc. Rev. 2010, 39, 558; for selected examples, see
20. P. Kwiatkowski, T. D. Beeson, J. C. Conrad, D. W. C. MacMillan, J. Am. Chem. Soc. 2011, 133, 1738
21. M. H. Sha, A. Katcher, A. G. Doyle, J. Am. Chem. Soc. 2011, 133, 15902
22. J. Erb, D. H. Paull, T. Dudding, L. Belding, T. Lectka, J. Am. Chem. Soc. 2011, 133, 7536.
23. O. Tamura, M. Hashimoto, Y. Kobayashi, T. Katoh, K. Nakatani, M. Kamada, I. Hayakawa, T. Akiba, S. Terashima, Tetrahedron Lett. 1992, 33, 3487.
24. A. Imura, M. Itoh, A. Miyadera, Tetrahedron: Asymmetry 1998, 9, 3047.
25. C. Ni, J. Hu, Synlett 2011, 770
26. J. Hu, J. Fluorine Chem. 2009, 130, 1130
27. J. Hu, W. Zhang, F. Wang, Chem. Commun. 2009, 7465
28. G. K. S. Prakash, J. Hu, Acc. Chem. Res. 2007, 40, 921
29. W. Zhang, C. Ni, J. Hu, Top. Curr. Chem. 2012, 308, 25.
30. C. Ni, Y. Li, J. Hu, J. Org. Chem. 2006, 71, 6829
31. C. Ni, Ph.D. Dissertation, Shanghai Institute of Organic Chemistry (China), 2008
32. C. Ni, J. Liu, L. Zhang, J. Hu, Angew. Chem. 2007, 119, 800
33. Angew. Chem. Int. Ed. 2007, 46, 786.
34. M. Reggelin, C. Zur, Synthesis 2000, 1
35. H. Okamura, C. Bolm, Chem. Lett. 2004, 33, 482
36. M. Harmata, Chemtracts Org. Chem. 2003, 16, 660.
37. C. Urban, F. Cadoret, J. Blazejewski, E. Magnier, Eur. J. Org. Chem. 2011, 4862
38. Y. Nomura, E. Tokunaga, N. Shibata, Angew. Chem. 2011, 123, 1925
39. Angew. Chem. Int. Ed. 2011, 50, 1885
40. R. Kowalczyk, A. J. F. Edmunds, R. G. Hall, C. Bolm, Org. Lett. 2011, 13, 768
41. S. Noritake, N. Shibata, S. Nakamura, T. Toru, M. Shiro, Eur. J. Org. Chem. 2008, 3465
42. N. V. Kondratendo, O. A. Radchenko, L. M. Yagupol'skii, Zh. Org. Khim. 1984, 2250
43. E. Magnier, C. Wakselman, Synthesis 2003, 565
44. M. L. Boys, E. W. Collington, H. Finch, S. Swanson, J. F. Whitehead, Tetrahedron Lett. 1988, 29, 3365
45. K. Adachi, S. Ishikara, JP 20030388769, 2003.
46. W. Zhang, W. Huang, J. Hu, Angew. Chem. 2009, 121, 10042
47. Angew. Chem. Int. Ed. 2009, 48, 9858
48. W. Zhang, F. Wang, J. Hu, Org. Lett. 2009, 11, 2109
49. W. Zhang, J. Hu, Adv. Synth. Catal. 2010, 352, 2799.
50. D. Craig, S. J. Gore, M. I. Lansdell, S. E. Lewis, A. V. W. Mayweg, A. J. P. Whitee, Chem. Commun. 2010, 46, 4991
51. D. Craig, N. J. Geach, C. J. Pearson, A. M. Z. Slawin, A. J. P. White, D. J. Williams, Tetrahedron 1995, 51, 6071.
52. S. Balasubramaniam, I. S. Aidhen, Synthesis 2008, 23, 3707
53. J. Singh, N. Satyamurthi, I. S. Aidhen, J. Prakt. Chem. 2000, 342, 340
54. M. Mentzel, H. M. R. Hoffmann, J. Prakt. Chem. 1997, 339, 517
55. M. P. Sibi, Org. Prep. Proced. Int. 1993, 25, 15.
56. T. Furukawa, N. Shibata, S. Mizuta, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. 2008, 120, 8171
57. Angew. Chem. Int. Ed. 2008, 47, 8051
58. S. Zhang, Y. Zhang, Y. Ji, H. Li, W. Wang, Chem. Commun. 2009, 4886.