Catalytic enantioselective one-pot aminoborylation of aldehydes: A strategy for construction of nonracemic α-amino boronates

Journal of the American Chemical Society

Volumn 135, Issue 25, 2013, Pages 9252-9254

  Hong, Kai ^a   Morken, James P ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC ADDITION; BORONATES; BORONIC ESTERS; DIBORATION; DOUBLE BONDS; ENANTIOSELECTIVE; ONE POT; PT-CATALYZED;

CHEMISTRY; SYNTHESIS (CHEMICAL);

ALDEHYDES;

ALDEHYDE; BORONIC ACID DERIVATIVE; ESTER DERIVATIVE; PLATINUM;

AMINOACYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; ENANTIOSELECTIVITY;

ALDEHYDES; BORONIC ACIDS; CATALYSIS; IMINES; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM;

EID: 84879537309     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja402569j     Document Type: Article

References (36)

1. Dick, L. R.; Fleming, P. E. Drug. Discovery Today 2010, 15, 243
2. Baker, S. J.; Tomsho, J. W.; Benkovic, S. J. Chem. Soc. Rev. 2011, 40, 4279
3. Yang, W.; Gao, X.; Wang, B. Med. Res. Rev. 2003, 23, 346
4. Adams, J.; Kauffman Cancer Inv. 2004, 22, 304
5. Gallerani, E.; Zucchetti, M.; Brunelli, D.; Marangon, E.; Noberasco, C.; Hess, D.; Delmonte, A.; Martinelli, G.; Böhm, S.; Driessen, C.; De Braud, F.; Marsoni, S.; Cereda, R.; Sala, F.; D'Incalci, M.; Sessa, C. Eur. J. Cancer 2013, 49, 290
6. Roemmele, R. C.; Christie, M. A. Org. Process Res. Dev. 2013, 17, 422
7. Awano, T.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2011, 133, 20738
8. Ohmura, T.; Awano, T.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 13191
9. Ohmura, T.; Awano, T.; Suginome, M. Chem. Lett. 2009, 38, 664
10. Matteson, D. S.; Sadhu, K. M. J. Am. Chem. Soc. 1981, 103, 5241
11. Matteson, D. S. Med. Res. Rev. 2008, 28, 233
12. Matteson, D. S. Chem. Rev. 1989, 89, 1535
13. Beenen, M. A.; An, C.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 6910
14. Solé, C.; Gulyás, H.; Fernández, E. Chem. Commun. 2012, 48, 3769
15. Zhang, S.-S.; Zhao, Y.-S.; Tian, P.; Lin, G.-Q. Synlett 2013, 24, 437
16. Kliman, L. T.; Mlynarski, S. N.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 13210
17. Kliman, L. T.; Mlynarski, S. N.; Ferris, G. E.; Morken, J. P. Angew. Chem., Int. Ed. 2012, 51, 521
18. Hong, K.; Morken, J. P. J. Org. Chem. 2011, 76, 9102
19. Schuster, C. H.; Li, B.; Morken, J. P. Angew. Chem., Int. Ed. 2011, 50, 7906
20. Burks, H. E.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 9134
21. Burks, H. E.; Liu, S.; Morken, J. P. J. Am. Chem. Soc. 2007, 129, 8766
22. Woodward, A.; Burks, H. E.; Chan, L. M.; Morken, J. P. Org. Lett. 2005, 7, 5505
23. Pelz, N.; Woodward, A. R.; Burks, H. E.; Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2004, 126, 16328
24. Jung, H.-Y.; Yun, J. Org. Lett. 2012, 14, 2606
25. Lee, Y.; Jang, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 18234
26. Takaya, J.; Iwasawa, N. ACS Catal. 2012, 9, 1993
27. Dang, L.; Lin, Z.; Marder, T. B. Chem. Commun. 2009, 3987
28. Ramírez, J.; Lillo, V.; Segarra, A. M.; Fernández, E. C. R. Chim. 2007, 10, 138
29. Burks, H. E.; Morken, J. P. Chem. Commun. 2007, 4717
30. Beletskaya, I. B.; Moberg, C. Chem. Rev. 2006, 106, 2320
31. Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271
32. Marder, T. B.; Norman, N. C. Top. Catal. 1998, 5, 63
33. For non-enantioselective catalytic diboration of an arylimine, see: Mann, G.; John, K. D.; Baker, R. T. Org. Lett. 2000, 2, 2105
34. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, Second ed.; Wiley and Sons: New York, 1991; p 377.
35. For the synthesis of silylimines, see: Lou, S.; Moquist, P. N.; Schaus, S. E. J. Am. Chem. Soc. 2007, 129, 15398
36. Ohmura, T.; Awano, T.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 13191