Synthesis of trans-2-(trifluoromethyl)cyclopropanes via suzuki reactions with an N-methyliminodiacetic acid boronate

Organic Letters

Volumn 15, Issue 17, 2013, Pages 4284-4287

  Duncton, Matthew A J ^a   Singh, Rajinder ^a  

^a RIGEL PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; ESTER; FLUORINATED HYDROCARBON; IMINO ACID; N METHYLDIGLYCINE; N-METHYLIMINODIACETIC ACID; PALLADIUM; TRANS 2 (TRIFLUOROMETHYL)CYCLOPROPYLBORONIC ACID N METHYLIMINODIACETIC ACID; TRANS-2-(TRIFLUOROMETHYL)CYCLOPROPYLBORONIC ACID N-METHYLIMINODIACETIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BORONIC ACIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLOPROPANES; ESTERS; HYDROCARBONS, FLUORINATED; IMINO ACIDS; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 84883763345     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401636d     Document Type: Article

References (42)

1. Salaun, J. Topics Curr. Chem. 2000, 207, 1
2. Yale, H. L. J. Med. Chem. 1959, 1, 121
3. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem Soc. Rev. 2008, 37, 320
4. Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950
5. Wuitschik, G.; Carreira, E. M.; Wagner, B.; Fischer, H.; Parrilla, I.; Schuler, F.; Rogers-Evans, M.; Muller, K. J. Med. Chem. 2010, 53, 3227
6. Kettle, J. G.; Ward, R. A.; Griffen, E. Med. Chem. Commun. 2010, 1, 331 and references cited therein
7. Kelly, M. G.; Kincaid, J.; Janagani, S.; Duncton, M. U.S. Patent 0205773, 2006
8. Chem. Abstr. 2006, 145, 336048.
9. Duncton, M. A. J.; Ayala, L.; Kaub, C.; Janagani, S.; Edwards, W. T.; Orike, N.; Ramamoorthy, K.; Kincaid, J.; Kelly, M. G. Tetrahedron Lett. 2010, 51, 1009
10. Lovering, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752
11. Lovering, F. Med. Chem. Commun. 2013, 4, 515
12. Clemons, P. A.; Bodycombe, N. E.; Carrinski, H. A.; Wilson, J. A.; Shamji, A. F.; Wagner, B. K.; Koehler, A. N.; Schreiber, S. L. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 18787
13. Barnes-Seeman, D.; Jain, M.; Bell, L.; Ferreira, S.; Cohen, S.; Chen, X. H.; Amin, J.; Snodgrass, B.; Hatsis, P. ACS Med. Chem. Lett. 2013, 4, 514
14. For a review on the synthesis of (trifluoromethyl)cyclopropanes, see: Grygorenko, O. O.; Artamonov, O. S.; Komarov, I. V.; Mykhailiuk, P. K. Tetrahedron 2011, 67, 803
15. Le Maux, P.; Juillard, S.; Simonneaux, G. Synthesis 2006, 1701
16. Mykhailiuk, P. K.; Afonin, S.; Ulrich, A. S.; Komarov, I. V. Synthesis 2008, 1757
17. Morandi, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 938
18. Risse, J.; Fernández-Zúmel, M. A.; Cudré, Y.; Severin, K. Org. Lett. 2012, 14, 3060
19. Lin, H.; Shen, Q.; Lu, L. J. Org. Chem. 2011, 76, 7359
20. Kasai, N.; Maeda, R.; Furuno, H.; Hanamoto, T. Synthesis 2012, 44, 3489
21. Duncton, M.; Singh, R. Patent WO 075316, 2012
22. Chem. Abstr. 2012, 157, 76933.
23. For a review on the benefits of boronic acid MIDA esters, see: Gillis, E. P.; Burke, M. D. Aldrichimica Acta 2009, 42, 17
24. Uno, B. C.; Gillis, E. P.; Burke, M. D. Tetrahedron 2009, 65, 3130
25. Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2007, 129, 6716
26. Mancilla, T.; Contreras, R.; Wrackmeyer, B. J. Organomet. Chem. 1986, 307, 1
27. Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2008, 130, 14084
28. Lee, S. J.; Gray, K. C.; Paek, J. S.; Burke, M. D. J. Am. Chem. Soc. 2008, 130, 466
29. Woerly, E. M.; Cherney, A. H.; Davis, E. K.; Burke, M. D. J. Am. Chem. Soc. 2010, 132, 6941
30. Lee, S. J.; Anderson, T. M.; Burke, M. D. Angew. Chem., Int. Ed. 2010, 49, 8860
31. Brak, K.; Ellman, J. A. Org. Lett. 2010, 12, 2004
32. Fujii, S.; Chang, S. Y.; Burke, M. D. Angew. Chem., Int. Ed. 2011, 50, 7862
33. Gray, K. C.; Palacios, D. S.; Dailey, I.; Endo, M. M.; Uno, B. E.; Wilcock, B. C.; Burke, M. D. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 2234
34. Grob, J. E.; Nunez, J.; Dechantsreiter, M. A.; Hamann, L. G. J. Org. Chem. 2011, 76, 10241
35. Wallace, D. J.; Chen, C. Tetrahedron Lett. 2002, 43, 6987
36. Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 13028
37. For a review, see: Gagnon, A.; Duplessis, M.; Fader, L. Org. Prep. Proced. Int. 2010, 42, 1 and references cited therein
38. Bemis, G. W.; Murcko, M. A. J. Med. Chem. 1996, 39, 2887
39. Knapp, D. M.; Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2009, 131, 6961
40. Lennox, A. J. J.; Lloyd-Jones, G. C. Israel J. Chem. 2010, 50, 664
41. Congreve, M.; Carr, R.; Murray, C.; Jhoti, H. Drug Discovery Today 2003, 8, 876
42. For asymmetric syntheses of 2-(trifluoromethyl)cyclopropanes, see ref 12a and Morandi, B.; Mariampillai, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 1101