(4+1) vs (4+2): Catalytic Intramolecular Coupling between Cyclobutanones and Trisubstituted Allenes via C-C Activation

Journal of the American Chemical Society

Volumn 137, Issue 42, 2015, Pages 13715-13721

  Zhou, Xuan ^a   Dong, Guangbin ^a  

^a University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ACTIVATION; CYCLIZATION; HYDROCARBONS; SCAFFOLDS;

BICYCLIC PRODUCTS; C-C ACTIVATIONS; CYCLOBUTANONES; INTRAMOLECULAR COUPLING; ONE-CARBON UNITS; PHOSPHORAMIDITE LIGANDS; QUATERNARY CARBON; RHODIUM-CATALYZED;

KETONES;

ALLENE DERIVATIVE; CARBON; CYCLOBUTANONE DERIVATIVE; FUNCTIONAL GROUP; PHOSPHORAMIDOUS ACID; POLYCYCLIC HYDROCARBON; RHODIUM; ALKADIENE; ALKANONE; ALKENE; AZEPINE DERIVATIVE; PROPADIENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; ENANTIOSELECTIVITY; CHEMISTRY; X RAY CRYSTALLOGRAPHY;

ALKADIENES; ALKENES; AZEPINES; BUTANONES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MOLECULAR STRUCTURE; RHODIUM;

EID: 84946072805     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b09799     Document Type: Article

References (61)

1. Jones, W. D. Nature 1993, 364, 676 10.1038/364676a0
2. Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97 10.1007/3-540-68525-1-5
3. Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870 10.1002/(SICI)1521-3773(19990401)38:7<870::AID-ANIE870>3.0.CO;2-3
4. Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610 10.1039/b308864m
5. Satoh, T.; Miura, M. Top. Organomet. Chem. 2005, 14, 1 10.1007/b104133
6. Necas, D.; Kotora, M. Curr. Org. Chem. 2007, 11, 1566 10.2174/138527207782418645
7. Crabtree, R. H. Chem. Rev. 1985, 85, 245 10.1021/cr00068a002
8. Ruhland, K. Eur. J. Org. Chem. 2012, 2012, 2683 10.1002/ejoc.201101616
9. Korotvicka, A.; Necas, D.; Kotora, M. Curr. Org. Chem. 2012, 16, 1170 10.2174/138527212800564213
10. Seiser, T.; Saget, T.; Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed. 2011, 50, 7740 10.1002/anie.201101053
11. Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 1100 10.1039/C0CC02566F
12. Dermenci, A.; Coe, P. W.; Dong, G. Org. Chem. Front. 2014, 1, 567 10.1039/c4qo00053f
13. C-C bond activation. In Topics in Current Chemistry; Dong, G., Ed.; Springer-Verlag: Berlin, 2014, Vol. 346.
14. Chen, F.; Wang, T.; Jiao, N. Chem. Rev. 2014, 114, 8613 10.1021/cr400628s
15. Souillart, L.; Cramer, N. Chem. Rev. 2015, 115, 9410 10.1021/acs.chemrev.5b00138
16. South, M. S.; Liebeskind, L. S. J. Am. Chem. Soc. 1984, 106, 4181 10.1021/ja00327a019
17. Murakami, M.; Itahashi, T.; Ito, Y. J. Am. Chem. Soc. 2002, 124, 13976 10.1021/ja021062n
18. Mei, G.; Liu, X.; Qiao, C.; Chen, W.; Li, C.-C. Angew. Chem., Int. Ed. 2015, 54, 1754 10.1002/anie.201410806
19. Kuwajima, I.; Tanino, K. Chem. Rev. 2005, 105, 4661 10.1021/cr040636z
20. Kim, S.; Winkler, J. Chem. Soc. Rev. 1997, 26, 387 10.1039/cs9972600387
21. Ylijoki, K. E. O.; Stryker, J. M. Chem. Rev. 2013, 113, 2244 10.1021/cr300087g
22. Murakami, M.; Ashida, S. Chem. Commun. 2006, 4599 10.1039/b611522e
23. Souillart, L.; Parker, E.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 9640 10.1002/anie.201405834
24. Souillart, L.; Cramer, N.; Parker, E. Angew. Chem., Int. Ed. 2014, 53, 3001 10.1002/anie.201311009
25. Parker, E.; Cramer, N. Organometallics 2014, 33, 780 10.1021/om4011627
26. Liu, L.; Ishida, N.; Murakami, M. Angew. Chem., Int. Ed. 2012, 51, 2485 10.1002/anie.201108446
27. Ko, H. M.; Dong, G. Nat. Chem. 2014, 6, 739 10.1038/nchem.1989
28. For a recent review of (4+1) transformation, see: Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Rev. 2015, 115, 5301 10.1021/cr5006974
29. López, F.; Mascareñas, J. L. Chem. Soc. Rev. 2014, 43, 2904 10.1039/c4cs00024b
30. Yu, S.; Ma, S. Angew. Chem., Int. Ed. 2012, 51, 3074 10.1002/anie.201101460
31. Croatt, M. P.; Wender, P. A. Eur. J. Org. Chem. 2010, 2010, 19 10.1002/ejoc.200900929
32. Kitagaki, S.; Inagaki, F.; Mukai, C. Yuki Gosei Kagaku Kyokaishi 2009, 67, 618 10.5059/yukigoseikyokaishi.67.618
33. Ma, S. Aldrichim. Acta 2007, 40, 91
34. Ma, S. Chem. Rev. 2005, 105, 2829 10.1021/cr020024j
35. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12 10.1039/b103904k
36. Ma, S.; Lu, P.; Lu, L.; Hou, H.; Wei, J.; He, Q.; Gu, Z.; Jiang, X.; Jin, X. Angew. Chem., Int. Ed. 2005, 44, 5275 10.1002/anie.200501350
37. Wender, P. A.; Deschamps, N. M.; Sun, R. Angew. Chem., Int. Ed. 2006, 45, 3957 10.1002/anie.200600806
38. Wender, P. A.; Croatt, M. P.; Deschamps, N. M. Angew. Chem., Int. Ed. 2006, 45, 2459 10.1002/anie.200600300
39. Trillo, B.; López, F.; Gulías, M.; Castedo, L.; Mascareñas, J. L. Angew. Chem., Int. Ed. 2008, 47, 951 10.1002/anie.200704566
40. Fujiwara, Y.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 12293 10.1021/ja2049012
41. Oonishi, Y.; Hosotani, A.; Sato, Y. J. Am. Chem. Soc. 2011, 133, 10386 10.1021/ja203824v
42. Shu, D.; Li, X.; Zhang, M.; Robichaux, P. J.; Tang, W. Angew. Chem., Int. Ed. 2011, 50, 1346 10.1002/anie.201006881
43. Evans, P. A.; Negru, D. E.; Shang, D. Angew. Chem., Int. Ed. 2015, 54, 4768 10.1002/anie.201410857
44. Mei, L. Y.; Wei, Y.; Tang, X. Y.; Shi, M. J. Am. Chem. Soc. 2015, 137, 8131 10.1021/jacs.5b02080
45. Casanova, N.; Seoane, A.; Mascareñas, J. L.; Gulías, M. Angew. Chem., Int. Ed. 2015, 54, 2374 10.1002/anie.201410350
46. Szeto, J.; Sriramurthy, V.; Kwon, O. Org. Lett. 2011, 13, 5420 10.1021/ol201730q
47. Kuppusamy, R.; Gandeepan, P.; Cheng, C.-H. Org. Lett. 2015, 17, 3846 10.1021/acs.orglett.5b01825
48. Xia, Y.; Liu, Z.; Liu, Z.; Ge, R.; Ye, F.; Hossain, M.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2014, 136, 3013 10.1021/ja500118w
49. Yada, A.; Fujita, S.; Murakami, M. J. Am. Chem. Soc. 2014, 136, 7217 10.1021/ja502229c
50. Davies, H. M. L. Aldrichim. Acta 1997, 30, 107
51. Davies, H. M. L. Curr. Org. Chem. 1998, 2, 463
52. Wang, X.; Xu, X.; Zavalij, P. Y.; Doyle, M. P. J. Am. Chem. Soc. 2011, 133, 16402 10.1021/ja207664r
53. Lian, Y.; Davies, H. M. L. J. Am. Chem. Soc. 2011, 133, 11940 10.1021/ja2051155
54. Shaw, M. H.; Melikhova, E. Y.; Kloer, D. P.; Whittingham, W. G.; Bower, J. F. J. Am. Chem. Soc. 2013, 135, 4992 10.1021/ja401936c
55. Shaw, M. H.; McCreanor, N. G.; Whittingham, W. G.; Bower, J. F. J. Am. Chem. Soc. 2015, 137, 463 10.1021/ja511335v
56. Hong, X.; Stevens, M. C.; Liu, P.; Wender, P. A.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 17273 10.1021/ja5098308
57. Feringa, B. L. Acc. Chem. Res. 2000, 33, 346 10.1021/ar990084k
58. Teichert, J. F.; Feringa, B. L. Angew. Chem., Int. Ed. 2010, 49, 2486 10.1002/anie.200904948
59. Matsuda, T.; Shigeno, M.; Murakami, M. Chem. Lett. 2006, 35, 288 10.1246/cl.2006.288
60. Matsuda, T.; Fujimoto, A.; Ishibashi, M.; Murakami, M. Chem. Lett. 2004, 33, 876 10.1246/cl.2004.876
61. Shaw, M. H.; Croft, R. A.; Whittingham, W. G.; Bower, J. F. J. Am. Chem. Soc. 2015, 137, 8054 10.1021/jacs.5b05215