A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes

Journal of the American Chemical Society

Volumn 137, Issue 43, 2015, Pages 13760-13763

  Jia, Tao ^a   Cao, Peng ^a   Wang, Bing ^a   Lou, Yazhou ^a   Yin, Xuemei ^a   Wang, Min ^a   Liao, Jian ^a  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBONS; STYRENE;

ALLYL CARBONATES; ALLYLBORATION; ANTIPSYCHOTIC DRUG; COOPERATIVE CATALYSIS; ENANTIOSELECTIVE; FUNCTIONALIZED; HIGH ENANTIOSELECTIVITY; THREE COMPONENT REACTIONS;

ENANTIOSELECTIVITY;

ALKENE DERIVATIVE; BORON; CARBONIC ACID DERIVATIVE; COPPER; PALLADIUM; PRECLAMOL; STYRENE DERIVATIVE; ALKENE; ALLYL COMPOUND; BORANE DERIVATIVE; ORGANOMETALLIC COMPOUND; PIPERIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; ENANTIOSELECTIVITY; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; ALLYL COMPOUNDS; BORANES; CATALYSIS; COPPER; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PIPERIDINES; STEREOISOMERISM;

EID: 84952896677     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b09146     Document Type: Article

References (47)

1. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417 10.1021/cr100327p
2. Li, J.; Grillo, A. S.; Burke, D. M. Acc. Chem. Res. 2015, 48, 2297 10.1021/acs.accounts.5b00128
3. Meng, F.; McGrath, K. P.; Hoveyda, A. H. Nature 2014, 513, 367 10.1038/nature13735
4. Balieu, S.; Hallett, G. E.; Burns, M.; Bootwicha, T.; Studley, J.; Aggarwal, V. K. J. Am. Chem. Soc. 2015, 137, 4398 10.1021/ja512875g
5. Blaisdell, T. P.; Morken, J. P. J. Am. Chem. Soc. 2015, 137, 8712 10.1021/jacs.5b05477
6. Semba, K.; Fujihara, T.; Terao, J.; Tsuji, Y. Tetrahedron 2015, 71, 2183 and references cited therein. 10.1016/j.tet.2015.02.027
7. Ito, H.; Kosaka, Y.; Nonoyama, K.; Sasaki, Y.; Sawamura, M. Angew. Chem., Int. Ed. 2008, 47, 7424 10.1002/anie.200802342
8. Zhong, C.; Kun, S.; Kosaka, Y.; Sawamura, M.; Ito, H. J. Am. Chem. Soc. 2010, 132, 11440 10.1021/ja103783p
9. Meng, F.; Jang, H.; Jung, B.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2013, 52, 5046 10.1002/anie.201301018
10. Liu, P.; Fukui, Y.; Tian, P.; He, Z.-T.; Sun, C.-Y.; Wu, N.-Y.; Lin, G.-Q. J. Am. Chem. Soc. 2013, 135, 11700 10.1021/ja404593c
11. Burns, A. R.; González, J. S.; Lam, H. W. Angew. Chem., Int. Ed. 2012, 51, 10827 10.1002/anie.201205899
12. Meng, F.; Haeffner, F.; Hoveyda, A. H. J. Am. Chem. Soc. 2014, 136, 11304 10.1021/ja5071202
13. Nelson, H. M.; Williams, B. D.; Miró, J.; Toste, F. D. J. Am. Chem. Soc. 2015, 137, 3213 10.1021/jacs.5b00344
14. Semba, K.; Nakao, Y. J. Am. Chem. Soc. 2014, 136, 7567 10.1021/ja5029556
15. Smith, K. B.; Logan, K. M.; You, W.; Brown, M. K. Chem.-Eur. J. 2014, 20, 12032 10.1002/chem.201404310
16. Logan, K. M.; Smith, K. B.; Brown, M. K. Angew. Chem., Int. Ed. 2015, 54, 5228 10.1002/anie.201500396
17. van den Beuken, E. K.; Feringa, B. L. Tetrahedron 1998, 54, 12985 10.1016/S0040-4020(98)00319-6
18. Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302 10.1039/b309033g
19. Park, J.; Hong, S. Chem. Soc. Rev. 2012, 41, 6931 10.1039/c2cs35129c
20. Allen, A. E.; MacMillan, D. W. C. Chem. Sci. 2012, 3, 633 10.1039/c2sc00907b
21. Chen, D.; Han, Z.; Zhou, X.; Gong, L. Acc. Chem. Res. 2014, 47, 2365 10.1021/ar500101a
22. Nahra, F.; Macé, Y.; Lambin, D.; Riant, O. Angew. Chem., Int. Ed. 2013, 52, 3208 10.1002/anie.201208612
23. Lee, Y.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 3160 10.1021/ja809382c
24. Corberán, R.; Mszar, N. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2011, 50, 7079 10.1002/anie.201102398
25. Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2013, 135, 4934 10.1021/ja4007645
26. Sakae, R.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2015, 54, 613 10.1002/anie.201409104
27. Christmann, M.; Brase, S. Asymmetric cross-coupling reactions Adv. Synth. Catal. 2008, 349, 1809 10.1002/adsc.200700251
28. Glasspoole, B. W.; Crudden, C. M. Nat. Chem. 2011, 3, 912 10.1038/nchem.1210
29. Swift, E.; Jarvo, E. R. Tetrahedron 2013, 69, 5799 10.1016/j.tet.2013.05.001
30. Molander, G. A. J. Org. Chem. 2015, 80, 7837 10.1021/acs.joc.5b00981
31. Leonori, D.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2015, 54, 1082 10.1002/anie.201407701
32. Wang, C. Y.; Dersa, J.; Biscoe, M. R. Chem. Sci. 2015, 6, 5105 10.1039/C5SC01710F
33. Cherney, A. H.; Kdunce, N. T.; Reisman, S. E. Chem. Rev. 2015, 115, 9587 10.1021/acs.chemrev.5b00162
34. Jia, T.; Cao, P.; Wang, D.; Lou, Y.; Liao, J. Chem.-Eur. J. 2015, 21, 4918 10.1002/chem.201500060
35. Wang, D.; Cao, P.; Wang, B.; Jia, T.; Lou, Y.; Wang, M.; Liao, J. Org. Lett. 2015, 17, 2420 10.1021/acs.orglett.5b00934
36. Lou, Y.; Cao, P.; Jia, T.; Zhang, Y.; Wang, M.; Liao, J. Angew. Chem., Int. Ed. 2015, 54, 12134 10.1002/anie.201505926
37. Yoshida, H.; Kageyuki, I.; Takaki, K. Org. Lett. 2013, 15, 952 10.1021/ol4001526
38. Kageyuki, I.; Yoshida, H.; Takaki, K. Synthesis 2014, 46, 1924 10.1055/s-0033-1341267
39. Lloyd-Jones, G. C.; Stephen, S. C. Chem.-Eur. J. 1998, 4, 2539 10.1002/(SICI)1521-3765(19981204)4:12<2539::AID-CHEM2539>3.0.CO;2-1
40. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1998, 120, 70 10.1021/ja9726522
41. Turnbull, B. W. H.; Evans, P. A. J. Am. Chem. Soc. 2015, 137, 6156 10.1021/jacs.5b02810
42. Jiao, Z. W.; Zhang, S. Y.; He, C.; Tu, Y. Q.; Wang, S. H.; Zhang, F. M.; Zhang, Y. Q.; Li, H. Angew. Chem., Int. Ed. 2012, 51, 8811 10.1002/anie.201204274
43. Mirabdolbaghi, R.; Dudding, T. Tetrahedron 2012, 68, 1988 10.1016/j.tet.2011.12.040
44. J, Y.; Sarlah, D.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 7644 10.1002/anie.201501851
45. Hu, J.; Lu, Y.; Li, Y.; Zhou, J. Chem. Commun. 2013, 49, 9425 10.1039/c3cc45233f
46. Macchia, M.; Cervetto, L.; Demontis, G. C.; Longoni, B.; Minutolo, F.; Orlandini, E.; Ortore, G.; Papi, C.; Sbrana, A.; Macchia, B. J. Med. Chem. 2003, 46, 161 10.1021/jm021019a
47. Pettersson, F.; Ponten, H.; Waters, N.; Waters, S.; Sonesson, C. J. Med. Chem. 2010, 53, 2510 10.1021/jm901689v