A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates

Journal of the American Chemical Society

Volumn 136, Issue 18, 2014, Pages 6534-6537

  Sun, Chunrui ^a   Potter, Bowman ^a   Morken, James P ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

ASYMMETRIC INDUCTION; CROSS-COUPLINGS; INVERSION OF CONFIGURATION; MONODENTATES; ORGANOBORONATES; PHOSPHORAMIDITE LIGANDS; SUZUKI REACTION; TRANSMETALATION;

CHEMISTRY;

BORIC ACID; BORONIC ACID DERIVATIVE; CARBON; LIGAND; ORGANOBORONIC ACID DERIVATIVE; PHOSPHORAMIDOUS ACID; UNCLASSIFIED DRUG; BORON; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; SUZUKI REACTION; CHEMISTRY; STEREOISOMERISM;

BORON; CATALYSIS; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 84900322702     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja500029w     Document Type: Article

References (57)

1. Hall, D. G. Boronic Acids, 2 nd ed.; Wiley-VCH: Weinheim, 2011.
2. Carroll, A.-M.; OSullivan, T. P.; Guiry, P. J. Adv. Synth. Catal. 2005, 347, 609
3. Lee, Y.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 3160
4. Noh, D.; Chea, H.; Ju, J.; Yun, J. Angew. Chem., Int. Ed. 2009, 48, 6062
5. Smith, S. M.; Takacs, J. M. J. Am. Chem. Soc. 2010, 132, 1740
6. Corberán, R.; Mszar, N. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2011, 50, 7079
7. Smith, S. M.; Hoang, G. L.; Pal, R.; Khaled, M. O. B.; Pelter, L. S.; Zeng, X. C.; Takacs, J. M. Chem. Commun. 2012, 48, 12180
8. For a review of catalytic enantioselective conjugate borylation, see: Calow, A. D. J.; Whiting, A. Org. Biomol. Chem. 2012, 10, 5485
9. Ito, H.; Ito, S.; Sasaki, Y.; Matsuura, K.; Sawamura, M. J. Am. Chem. Soc. 2007, 129, 14856
10. Guzman-Martinez, A.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10634
11. Ito, H.; Kunii, S.; Sawamura, M. Nat. Chem. 2010, 2, 972
12. Park, J. K.; Lackey, H. H.; Ondrusek, B. A.; McQuade, D. T. J. Am. Chem. Soc. 2011, 133, 2410
13. Lee, J. C. H.; Hall, D. G. J. Am. Chem. Soc. 2010, 132, 5544
14. Carosi, L.; Hall, D. G. Angew. Chem., Int. Ed. 2007, 46, 5913
15. Gao, X.; Hall, D. G. J. Am. Chem. Soc. 2003, 125, 9308
16. Ding, J.; Lee, J. C. H.; Hall, D. G. Org. Lett. 2012, 14, 4462
17. Morgan, J. B.; Morken, J. P. J. Am. Chem. Soc. 2004, 126, 15338
18. Moran, W. J.; Morken, J. P. Org. Lett. 2006, 8, 2413
19. Paptchikhine, A.; Cheruku, P.; Engman, M.; Andersson, P. G. Chem. Commun. 2009, 5996
20. Ganic, A.; Pfaltz, A. Chem. - Eur. J. 2012, 18, 6724
21. Gazic Smilovic, I.; Casas-Arcé, E.; Roseblade, S. J.; Nettekoven, U.; Zanotti-Gerosa, A.; Kovačevič, M.; Časar, Z. Angew. Chem., Int. Ed. 2012, 51, 1014
22. Morgan, J. B.; Miller, S. P.; Morken, J. P. J. Am. Chem. Soc. 2003, 125, 8702
23. Trudeau, S.; Morgan, J. B.; Shrestha, M.; Morken, J. P. J. Org. Chem. 2005, 70, 9538
24. Pelz, N. F.; Woodward, A. R.; Burks, H. E.; Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2004, 126, 16328
25. Burks, H. E.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 9134
26. Kliman, L. T.; Mlynarski, S. N.; Morken, J. P. J. Am. Chem. Soc. 2010, 132, 13949
27. Coombs, J. R.; Haeffner, F.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2013, 135, 11222
28. Toribatake, K.; Nishiyama, H. Angew. Chem., Int. Ed. 2013, 52, 11011
29. Lee, Y.; Jang, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 18234
30. Mlynarski, S. N.; Schuster, C. H.; Morken, J. P. Nature 2014, 505, 386
31. Endo, K.; Ohkubo, T.; Hirokami, M.; Shibata, T. J. Am. Chem. Soc. 2010, 132, 11033
32. Endo, K.; Ohkubo, T.; Shibata, T. Org. Lett. 2011, 13, 3368
33. Endo, K.; Ohkubo, T.; Ishioka, T.; Shibata, T. J. Org. Chem. 2012, 77, 4826
34. Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894
35. Feng, X.; Jeon, H.; Yun, J. Angew. Chem., Int. Ed. 2013, 52, 3989
36. Cho, S. Y.; Shibasaki, M. Tetrahedron: Asymmetry 1998, 9, 3751
37. Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765
38. Matteson, D. S.; Moody, R. J. Organometallics 1982, 1, 20
39. Ito, H.; Kubota, K. Org. Lett. 2012, 14, 890
40. Nilvebrant, L.; Andersson, K.-E.; Gillberg, P.-G.; Stahl, M.; Sparf, B. Eur. J. Pharmacol. 1997, 327, 195
41. Andersson, P. G.; Schink, H. E.; Österlund, K. J. Org. Chem. 1998, 63, 8067
42. Hedberg, C.; Andersson, P. G. Adv. Synth. Catal. 2005, 347, 662
43. Ulgheri, F.; Marchetti, M.; Piccolo, O. J. Org. Chem. 2007, 72, 6056
44. Botteghi, C.; Corrias, T.; Marchetti, M.; Paganelli, S.; Piccolo, O. Org. Process Res. Dev. 2002, 6, 379
45. Chen, G.; Tokunaga, N.; Hayashi, T. Org. Lett. 2005, 7 (11) 2285
46. Roesner, S.; Aggarwal, V. K. Can. J. Chem. 2012, 90, 965
47. Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024
48. Jonsson, N. A.; Sparf, B. A.; Mikiver, L.; Moses, P.; Nilvebrant, L.; Glas, G. U.S. Patent 5,382,600 A1, 1995.
49. Amatore, C.; Jutand, A.; Le Duc, G. Chem. - Eur. J. 2011, 17, 2492
50. Carrow, B.; Hartwig, J. J. Am. Chem. Soc. 2011, 133, 2116
51. Suzaki, Y.; Osakada, K. Organometallics 2006, 25, 3251
52. Braga, A. A.; Morgon, N. H.; Ujaque, G.; Maseras, F. J. Am. Chem. Soc. 2005, 127, 9298
53. Ohmura, T.; Awano, T.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 13191
54. Sandrock, D. L.; Jean-Gérard, L.; Chen, C. Y.; Dreher, S. D.; Molander, G. A. J. Am. Chem. Soc. 2010, 17108
55. Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129
56. Kells, K. W.; Chong, J. M. J. Am. Chem. Soc. 2004, 126, 15666
57. Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793