Asymmetric electrophilic fluorocyclization with carbon nucleophiles

Angewandte Chemie - International Edition

Volumn 52, Issue 37, 2013, Pages 9796-9800

  Wolstenhulme, Jamie R ^a   Rosenqvist, Jessica ^a   Lozano, Oscar ^a   Ilupeju, John ^a   Wurz, Nathalie ^a   Engle, Keary M ^a   Pidgeon, George W ^a   Moore, Peter R ^b   Sandford, Graham ^c   Gouverneur, Véronique ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c DURHAM UNIVERSITY   (United Kingdom)

Author keywords

asymmetric synthesis; cyclization; fluorine; helical structures; synthetic methods

Indexed keywords

ASYMMETRIC SYNTHESIS; ASYMMETRIC VARIANTS; CARBON NUCLEOPHILES; FLUORINE TRANSFERS; HELICAL STRUCTURES; PROCHIRAL ALKENES; SELECTFLUOR; SYNTHETIC METHODS;

CHEMICAL COMPOUNDS; CYCLIZATION; FLUORINE;

STEREOCHEMISTRY;

CARBON; FLUORINE; METAL; PYRIDINIUM DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMISTRY; CONFORMATION; CYCLIZATION; HELICAL STRUCTURES; STEREOISOMERISM; SYNTHETIC METHODS; X RAY CRYSTALLOGRAPHY;

ASYMMETRIC SYNTHESIS; CYCLIZATION; FLUORINE; HELICAL STRUCTURES; SYNTHETIC METHODS;

CARBON; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; FLUORINE; METALS; MOLECULAR CONFORMATION; PYRIDINIUM COMPOUNDS; STEREOISOMERISM;

EID: 84883501876     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201304845     Document Type: Article

References (41)

1. J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote, M. R. Prinsep, Nat. Prod. Rep. 2006, 23, 26-78
2. H. Ishibashi, K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 11122-11123
3. R. A. Yoder, J. N. Johnston, Chem. Rev. 2005, 105, 4730-4756
4. A. X. Huang, Z. Xiong, E. J. Corey, J. Am. Chem. Soc. 1999, 121, 9999-10003
5. J. N. Carter-Franklin, J. D. Parrish, R. A. Tschirret-Guth, R. D. Little, A. Butler, J. Am. Chem. Soc. 2003, 125, 3688-3689; for selected reviews on halocyclizations, see
6. S. E. Denmark, W. E. Kuester, M. T. Burk, Angew. Chem. 2012, 124, 11098-11113
7. Angew. Chem. Int. Ed. 2012, 51, 10938-10953
8. A. Castellanos, S. P. Fletcher, Chem. Eur. J. 2011, 17, 5766-5776.
9. A. Sakakura, A. Ukai, K. Ishihara, Nature 2007, 445, 900-903.
10. S. A. Snyder, D. S. Treitler, Angew. Chem. 2009, 121, 8039-8043
11. Angew. Chem. Int. Ed. 2009, 48, 7899-7903
12. S. A. Snyder, D. S. Treitler, A. P. Brucks, J. Am. Chem. Soc. 2010, 132, 14303-14314.
13. N. A. Cochrane, H. Nguyen, M. R. Gagné, J. Am. Chem. Soc. 2013, 135, 628-631.
14. S. C. Wilkinson, R. Salmon, V. Gouverneur, Future Med. Chem. 2009, 1, 847-863. For π cyclizations followed by diastereoselective electrophilic fluorination, see
15. J. Nie, H.-W. Zhu, H.-F. Cui, M.-Q. Hua, J.-A. Ma, Org. Lett. 2007, 9, 3053-3056
16. W.-T. Meng, Y. Zheng, J. Nie, H.-Y. Xiong, J.-A. Ma, J. Org. Chem. 2013, 78, 559-567.
17. S. Stavber, T. S. Pecǎn, M. Papež, M. Zupan, Chem. Commun. 1996, 2247-2248.
18. W. Wang, B. Xu, G. B. Hammond, Synthesis 2011, 2383-2386.
19. D. Cahard, C. Audouard, J.-C. Plaquevent, N. Roques, Org. Lett. 2000, 2, 3699-3701
20. N. Shibata, E. Suzuki, Y. Takeuchi, J. Am. Chem. Soc. 2000, 122, 10728-10729
21. T. Ishimaru, N. Shibata, T. Horikawa, N. Yasuda, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. 2008, 120, 4225-4229
22. Angew. Chem. Int. Ed. 2008, 47, 4157-4161; for other chiral N-F reagents, see
23. Y. Takeuchi, T. Suzuki, A. Satoh, T. Shiragami, N. Shibata, J. Org. Chem. 1999, 64, 5708-5711
24. N. Shibata, Z. Liu, Y. Takeuchi, Chem. Pharm. Bull. 2000, 48, 1954-1958
25. N. Shibata, E. Suzuki, T. Asahi, M. Shiro, J. Am. Chem. Soc. 2001, 123, 7001-7009.
26. S. C. Wilkinson, O. Lozano, M. Schuler, M. C. Pacheco, R. Salmon, V. Gouverneur, Angew. Chem. 2009, 121, 7217-7220
27. Angew. Chem. Int. Ed. 2009, 48, 7083-7086.
28. O. Lozano, G. Blessley, T. Martinez del Campo, A. L. Thompson, G. T. Giuffredi, M. Bettati, M. Walker, R. Borman, V. Gouverneur, Angew. Chem. 2011, 123, 8255-8259
29. Angew. Chem. Int. Ed. 2011, 50, 8105-8109.
30. R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem. 2012, 4, 603-614
31. M. Mahlau, B. List, Angew. Chem. 2013, 125, 540-556
32. Angew. Chem. Int. Ed. 2013, 52, 518-533.
33. V. Rauniyar, A. D. Lackner, G. L. Hamilton, F. D. Toste, Science 2011, 334, 1681-1684
34. R. J. Phipps, K. Hiramatsu, F. D. Toste, J. Am. Chem. Soc. 2012, 134, 8376-8379
35. T. Honjo, R. J. Phipps, V. Rauniyar, F. D. Toste, Angew. Chem. 2012, 124, 9822-9826
36. Angew. Chem. Int. Ed. 2012, 51, 9684-9688
37. R. J. Phipps, F. D. Toste, J. Am. Chem. Soc. 2013, 135, 1268-1271.
38. R. Oi, K. B. Sharpless, Tetrahedron Lett. 1991, 32, 4853-4854.
39. T. Umemoto, K. Harasawa, G. Tomizawa, J. Fluorine Chem. 1991, 53, 369-377.
40. The structures of 2 d, 2 g, and 2 i were determined by single-crystal X-ray diffraction. CCDC 950529 (2 d), CCDC 950530 (2 g), and CCDC 950531 (2 i) contain 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.
41. W. E. Kowtoniuk, D. K. MacFarland, G. N. Grover, Tetrahedron Lett. 2005, 46, 5703-5705.