Enantioselective β-boration of acyclic enones by a [2.2]paracyclophane-based N-heterocyclic carbene copper(I) catalyst

Journal of Organic Chemistry

Volumn 78, Issue 4, 2013, Pages 1677-1681

  Zhao, Lei ^a   Ma, Yudao ^a   He, Fuyan ^a   Duan, Wenzeng ^a   Chen, Jianqiang ^a   Song, Chun ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

[2.2]PARACYCLOPHANE; ACYCLIC ENONES; COPPER (I) COMPLEXES; COPPER CATALYST; EFFICIENT CATALYSTS; ENANTIOSELECTIVE; HIGH YIELD; N-HETEROCYCLIC CARBENES;

CATALYSTS; COPPER COMPOUNDS; ENANTIOSELECTIVITY; KETONES;

ORGANIC COMPOUNDS;

1 (4 FLUOROPHENYL) 3 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PROPAN 1 ONE; 1 (4 METHOXYPHENYL) 3 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PROPAN 1 ONE; 1 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLAN 2 YL) 1 4 TOLYLPROPAN 1 ONE; 1 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLAN 2 YL) 3 4 TOLYLPROPAN 1 ONE; 1 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLAN 2 YL)BUTAN 1 ONE; 1,3 DIPHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXIBOROLAN 2YL)PROPAN 1 ONE; 3 (2 CHLOROPHENYL) 1 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLAN 2 YL)PROPAN 1 ONE; 3 (2 METHOXYPHENYL) 1 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLAN 2 YL)PROPAN 1 ONE; 3 (3 CHLOROPHENYL) 1 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLAN 2 YL)PROPAN 1 ONE; 3 (3 METHOXYPHENYL) 1 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLAN 2 YL)PROPAN 1 ONE; 3 (4 CHLOROPHENYL) 1 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLAN 2 YL)PROPAN 1 ONE; 3 (4 METHOXYPHENYL) 1 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLAN 2 YL)PROPAN 1 ONE; 3 (FURAN 2 YL) 1 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLAN 2 YL)PROPAN 1 ONE; 3 (NAPHTHALEN 1 YL) 1 PHENYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PROPAN 1 ONE; 4 PHENYL 4 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOBOROLAN 2 YL)BUTAN 2 ONE; 4,4 DIMETHYL 1 PHENYL 1 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXOABOROLAN 2 YL)PENTAN 3 ONE; CARBENE; COPPER; COPPER COMPLEX; COPPER OXIDE; KETONE; N HETEROCYCLIC CARBENE COPPER COMPLEX; ORGANOBORON DERIVATIVE; TOLUENE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BORATION; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 84873948278     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302694d     Document Type: Article

References (49)

1. Hall, D. G. Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2 nd ed.; Wiley-VCH GmbH & Co.: Weinheim, 2011.
2. Scott, H. K.; Aggarwal, V. K. Chem.-Eur. J. 2011, 17, 13124
3. Smith, S. M.; Thacker, N. C.; Takacs, J. M. J. Am. Chem. Soc. 2008, 130, 3734
4. Burks, H. E.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 9134
5. Noh, D.; Chea, H.; Ju, J.; Yun, J. Angew. Chem., Int. Ed. 2009, 48, 6062
6. Lee, Y.; Jang, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 18234
7. Sasaki, Y.; Zhong, C.; Sawamura, M.; Ito, H. J. Am. Chem. Soc. 2010, 132, 1226
8. Park, J. K.; Lackey, H. H.; Ondrusek, B. A.; McQuade, D. T. J. Am. Chem. Soc. 2011, 133, 2410
9. Ibrahem, I.; Breistein, P.; Córdova, A. Angew. Chem., Int. Ed. 2011, 50, 12036
10. Schiffner, J. A.; Müther, K.; Oestreich, M. Angew. Chem., Int. Ed. 2010, 49, 1194
11. Hartmann, E.; Vyas, D. J.; Oestreich, M. Chem. Commun. 2011, 47, 7917
12. Sole, C.; Gulyas, H.; Fernández, E. Chem. Commun. 2012, 48, 3769
13. Sole, C.; Bonet, A.; de Vries, A. H. M.; de Vries, J. G.; Lefort, L.; Gulyas, H.; Fernández, E. Organometallic 2012, 31, 7855
14. Kleeberg, C.; Crawford, A. G.; Batsanov, A.S.; Hodgkinson, P. D.; Apperley, C.; Cheung, M. S.; Lin, Z.; Marder, T. B. J. Org. Chem. 2012, 77, 785
15. Kobayashi, S.; Xu, P.; Endo, T.; Ueno, M.; Kitanosono, T. Angew. Chem., Int. Ed. 2012, 51, 12763
16. Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612
17. Cohen, D. T.; Scheidt, K. A. Chem. Sci. 2012, 3, 53
18. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511
19. Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314
20. Lillo, V.; Prieto, A.; Bonet, A.; Díaz-Requejo, M. M.; Ramírez, J.; Pérez, P. J.; Fernández, E. Organometallics 2009, 28, 659
21. Park, J. K.; Lackey, H. H.; Rexford, M. D.; Kovnir, K.; Shatruk, M.; McQuade, D. T. Org. Lett. 2010, 12, 5008
22. H.-Weil, D.; Abboud, K. A.; Hong, S. Chem. Commun. 2010, 46, 7525
23. Hong, B.; Ma, Y.; Zhao, L.; Duan, W.; He, F.; Song, C. Tetrahedron: Asymmetry 2011, 22, 1055
24. Wu, H.; Radomkit, S.; O'Brien, J. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2012, 134, 8277
25. Zhao, L.; Ma, Y.; Duan, W.; He, F.; Chen, J.; Song, C. Org. Lett. 2012, 14, 5780
26. He, L.; Zhang, Y. R.; Huang, X. L.; Ye, S. Synthesis 2008, 17, 2825
27. Enders, D.; Han, J. Tetrahedron: Asymmetry 2008, 19, 1367
28. Shao, P. L.; Chen, X. Y.; Ye, S. Angew. Chem., Int. Ed. 2010, 122, 8590
29. Sun, L. H.; Shen, L. T.; Ye, S. Chem. Commun. 2011, 47, 10136
30. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Org. Chem. 2005, 70, 5725
31. Takikawa, H.; Suzuki, K. Org. Lett. 2007, 9, 2713
32. Allen, S. E.; Mahatthananchai, J.; Bode, J. W.; Kozlowski, M. C. J. Am. Chem. Soc. 2012, 134, 12098
33. Ma, Y.; Wei, S.; Wu, J.; Yang, F.; Liu, B.; Lan, J.; Yang, S.; You, J. Adv. Synth. Catal. 2008, 350, 2645
34. Struble, J. R.; Bode, J. W. Org. Synth. 2010, 87, 362
35. Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207
36. Hermanns, N.; Dahmen, S.; Bolm, C.; Bräse, S. Angew. Chem., Int. Ed. 2002, 41, 3692
37. Dahmen, S.; Bräse, S. J. Am. Chem. Soc. 2002, 124, 5940
38. Gibson, S. E.; Knight, J. D. Org. Biomol. Chem. 2003, 1, 1256
39. Bolm, C.; Focken, T.; Raabe, G. Tetrahedron: Asymmetry 2003, 14, 1733
40. Wu, X.-W.; Zhang, T.-Z.; Hou, X.-L. Tetrahedron: Asymmetry 2004, 15, 2357
41. Whelligan, D. K.; Bolm, C. J. Org. Chem. 2006, 71, 4609
42. Fürstner, A.; Alcarazo, M.; Krause, H.; Lehmann, C. W. J. Am. Chem. Soc. 2007, 129, 12676
43. Jiang, B.; Lei, Y.; Zhao, X. L. J. Org. Chem. 2008, 73, 7833
44. Aly, A. A.; Brown, A. B. Tetrahedron 2009, 65, 8055
45. Schneider, J. F.; Falk, F. C.; Fröhlich, R.; Paradies, J. Eur. J. Org. Chem. 2010, 2265
46. Gleiter, R.; Hopf, H. Modern Cyclophane Chemistry; Wiley-VCH: Weinheim, 2004.
47. Francos, J.; Grande-Carmona, F.; Faustino, H.; Iglesias-Sigüenaz, J.; Díez, E.; Alonso, I.; Fernádez, R.; Lassaletta, J. M.; López, F.; Mascareñas, J. L. J. Am. Chem. Soc. 2012, 134, 14322
48. Sim, H. S.; Feng, X.; Yun, J. Chem.-Eur. J. 2009, 15, 1939
49. Denmark, S. E.; Stavenger, R. A.; Wong, K. T. J. Org. Chem. 1998, 63, 9