Primary alkylboronic acids as highly active catalysts for the dehydrative amide condensation of α-hydroxycarboxylic acids

Organic Letters

Volumn 15, Issue 14, 2013, Pages 3654-3657

  Yamashita, Risa ^a   Sakakura, Akira ^b   Ishihara, Kazuaki ^a,c  

^a NAGOYA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BORON DERIVATIVE; BORONIC ACID DERIVATIVE; CARBOXYLIC ACID; N BUTYLBORONIC ACID; N-BUTYLBORONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

AMIDES; BORON COMPOUNDS; BORONIC ACIDS; CARBOXYLIC ACIDS; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84880520384     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401537f     Document Type: Article

References (35)

1. Charville, H.; Jackson, D.; Hodges, G.; Whiting, A. Chem. Commun. 2010, 46, 1813
2. Ishihara, K. Tetrahedron 2009, 65, 1085
3. Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606
4. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337
5. Montalbetti, C. A. G. N.; Falque, V. Tetrahedron 2005, 61, 10827
6. Maki, T.; Ishihara, K.; Yamamoto, H. Tetrahedron 2007, 63, 8645
7. Maki, T.; Ishihara, K.; Yamamoto, H. Org. Lett. 2006, 8, 1431
8. Maki, T.; Ishihara, K.; Yamamoto, H. Org. Lett. 2005, 7, 5043
9. Ishihara, K.; Ohara, S.; Yamamoto, H. Org. Synth. 2002, 79, 176
10. Ishihara, K.; Ohara, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 4196
11. Arnold, K.; Davies, B.; Giles, R. L.; Grosjean, C.; Smith, G. E.; Whiting, A. Adv. Synth. Catal. 2006, 348, 813
12. Arnold, K.; Batsanov, A. S.; Davies, B.; Whiting, A. Green Chem. 2008, 10, 124
13. Georgiou, I.; Ilyashenko, G.; Whiting, A. Acc. Chem. Res. 2009, 42, 756
14. Gernigon, N.; Al-Zoubi, R. M.; Hall, D. G. J. Org. Chem. 2012, 77, 8386
15. Al-Zoubi, R. M.; Marion, O.; Hall, D. G. Angew. Chem., Int. Ed. 2008, 47, 2876
16. Mylavarapu, R. K.; GCM, K.; Kolla, N.; Veeramalla, R.; Koilkonda, P.; Bhattacharya, A.; Bandichhor, R. Org. Process Res. Dev. 2007, 11, 1065
17. Tang, P. Org. Synth. 2005, 81, 262
18. Levonis, S. M.; Bornaghi, L. F.; Houston, T. A. Aust. J. Chem. 2007, 60, 821
19. Maki, T.; Ishihara, K.; Yamamoto, H. Org. Lett. 2005, 7, 5047
20. Houston, T. A.; Wilkinson, B. L.; Blanchfield, J. T. Org. Lett. 2004, 6, 679
21. For the boric acid catalyzed transamidation, see: Nguyen, T. B.; Sorres, J.; Tran, M. Q.; Ermolenko, L.; Al-Mourabit, A. Org. Lett. 2012, 14, 3202
22. Sakakura, A.; Yamashita, R.; Ohkubo, T.; Akakura, M.; Ishihara, K. Aust. J. Chem. 2011, 64, 1458
23. Sakakura, A.; Ohkubo, T.; Yamashita, R.; Akakura, M.; Ishihara, K. Org. Lett. 2011, 13, 892
24. Ishihara, K. In Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005; pp 1-99.
25. Boronate V should be much less reactive than I due to the strong coordination of hydroxide anion. Marcelli, T. Angew. Chem., Int. Ed. 2010, 49, 6840
26. CCDC-933866 contains supplementary crystallographic data for this paper. This information can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif. See the Supporting Information for details.
27. For another methodology of the synthesis of α-hydroxyamides, see: Leighty, M. W.; Shen, B.; Johnston, J. N. J. Am. Chem. Soc. 2012, 134, 15233
28. Bristow, M. R.; Hershberger, R. E.; Port, J. D.; Minobe, W.; Rasmussen, R. Mol. Pharmacol. 1989, 35, 295
29. Yokoyama, H.; Yanagisawa, T.; Taira, N. J. Cardiovasc. Pharmacol. 1988, 12, 323
30. Naito, K.; Nagao, T.; Ono, Y.; Otsuka, M.; Harigaya, S.; Nakajima, H. Jpn. J. Pharmacol. 1985, 39, 541
31. Naito, K.; Nagao, T.; Otsuka, M.; Harigaya, S.; Nakajima, H. Jpn. J. Pharmacol. 1985, 38, 235
32. Ikeo, T.; Nagao, T.; Suzuki, T.; Yabana, H.; Nakajima, H. Jpn. J. Pharmacol. 1985, 39, 191
33. Brown, R. F. C.; Donohue, A. C.; Jackson, W. R.; McCarthy, T. D. Tetrahedron 1994, 50, 13739
34. Jian-Xin, G.; Zu-Li, L.; Gou-Qiang, L. Tetrahedron 1993, 49, 5805
35. Corey, E. J.; Link, J. O. J. Org. Chem. 1991, 56, 442