Condensation reactions to form oxazoline-substituted potassium organotrifluoroborates

Organic Letters

Volumn 11, Issue 17, 2009, Pages 3830-3833

  Molander, Gary A ^a   Febo Ayala, Wilma ^a   Jean Gérard, Ludivine ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORIC ACID; OXAZOLE DERIVATIVE; POTASSIUM;

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

BORATES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; OXAZOLES; POTASSIUM;

EID: 69449101148     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901395c     Document Type: Article

References (30)

1. Wong, G. S. K.; Wu, W. 2-Oxazolines. In The Chemistry of Heterocyclic Compounds; Palmer, D. C. Eds.; Oxazoles: Synthesis, Reactions and Spectroscopy, Part B; John Wiley: Hoboken, 2004; Vol. 60, pp 331-513.
2. Wipf, P. Chem. Rev. 1995, 95, 2115-2134.
3. (a) Hayashi, T.; Uozumi, Y.; Yamazaki, A. Tetrahedron Lett. 1991, 32, 2799-2802.
4. (b) Soloshonok, V. A.; Hayashi, T. Tetrahedron Lett. 1994, 35, 2713-2716.
5. (c) Le Merrer, Y.; Gravier-Pelletier, C.; Gerrouache, M.; Depezay, J.-C. Tetrahedron Lett. 1998, 39, 385-388.
6. (d) Benito-Garagorri, D.; Bocokiæ, V.; Kirchner, K. Tetrahedron Lett. 2006, 47, 8641-8644.
7. (e) Shinada, T.; Ikebe, E.; Oe, K.; Namba, K.; Kawasaki, M.; Ohfune, Y. Org. Lett. 2007, 9, 1765-1767.
8. (f) Gosiewska, S.; Herreras Martínez, S.; Lutz, M.; Spek, A. L.; van Koten, G.; Klein Gebbink, R. J. M. Eur. J. Inorg. Chem. 2006, 4600-4607.
9. (g) Reetz, M. T.; Wünsch, T.; Harms, K. Tetrahedron Lett. 1989, 30, 3877-3880.
10. (h) Ortuno, J.-C.; Langlois, Y. Tetrahedron Lett. 1991, 32, 4491-4494.
11. (a) Darses, S.; Genêt, J.-P. Chem. Rev. 2008, 108, 288-325.
12. (b) Molander, G. A.; Ellis, N. Ace Chem. Res. 2007, 40, 275-286.
13. Molander, G. A.; Canturk, B.; Kennedy, L. E. J. Org. Chem. 2009, 74, 973-980, and references cited therein.
14. Molander, G. A.; Ham, J Org. Lett. 2006, 8, 2767-2770.
15. van Leusen, A. M.; Hoogenboom, B. E.; Siderius, H. Tetrahedron Lett. 1972, 23, 2369-2372.
16. DBU stands for 1, 8-diazabicyclo[5.4.0]undec-7-ene.
17. 3, DIPEA, guanidine, DABCO, and KCN. Other solvents tested were methanol, ethanol, DME, and DMSO, but they resulted in very impure product.
18. Tomoi, M.; Kato, Y.; Kakiuchi, H. Makromol. Chem. 1984, 185, 2117-2124.
19. (a) Ferrer Flegeau, E.; Popkin, M. E.; Greaney, M. F. J. Org. Chem. 2008, 73, 3303-3306.
20. (b) Araki, H.; Katoh, T.; Inoue, M. Tetrahedron Lett. 2007, 48, 3713-3717.
21. (c) Inoue, M. Mini-Rev. Org. Chem 2008, 5, 77-84, and references cited therein.
22. (a) Tyrell, E.; Brookes, P. Synthesis 2003, 469-483.
23. (b) Knapp, D. M.; Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2009, 131, 6961-6963.
24. For Suzuki-Miyaura cross-couplings of 4, 5-disubstituted oxazoles see: (a) Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2002, 4, 2905-2907.
25. (b) Vachal, P.; Toth, L. M. Tetrahedron Lett. 2004, 45, 7157-7161.
26. (c) Ferrer Flegeau, E.; Popkin, M. E.; Greaney, M. F. Org. Lett. 2006, 8, 2495-2498.
27. (d) Li, B.; Buzon, R. A.; Zhang, Z. Org. Proc. Res. Dev. 2007, 11, 951-955, and references cited therein.
28. Araki, H.; Katoh, T.; Inoue, M. Synlett 2006, 4, 555-558.
29. 3].
30. Rudi, A.; Stein, Z.; Green, S.; Goldberg, I.; Kashman, Y.; Benayahu, Y.; Schleyer, M. Tetrahedron Lett. 1994, 35, 2589-2592.