Copper-catalyzed regio- and stereoselective intermolecular three-component oxyarylation of allenes

Organic Letters

Volumn 16, Issue 10, 2014, Pages 2736-2739

  Itoh, Taisuke ^a   Shimizu, Yohei ^a   Kanai, Motomu ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLENE; BORONIC ACID DERIVATIVE; COPPER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKADIENES; BORONIC ACIDS; CATALYSIS; COPPER; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84900846913     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501022d     Document Type: Article

References (34)

1. Wolfe, J. P. Synlett 2008, 2913-2937
2. Hayashi, S.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2009, 131, 2052-2053
3. Zhang, G.; Wang, Y.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 1474-1475
4. Pathak, T. P.; Gligorich, K. M.; Welm, B. E.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 7870-7871
5. Miller, Y.; Miao, L.; Hosseini, A. S.; Chemler, S. R. J. Am. Chem. Soc. 2012, 134, 12149-12156
6. Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 12462-12465
7. Cahard, E.; Bremeyer, N.; Gaunt, M. J. Angew. Chem., Int. Ed. 2013, 52, 9284-9288
8. Graham, T. H.; Jones, C. M.; Jui, N. T.; MacMillan, D. W. C. J. Am. Chem. Soc. 2008, 130, 16494-16495
9. Melhado, A. D.; Brenzovich, W. E., Jr.; Lackner, A. D.; Toste, F. D. J. Am. Chem. Soc. 2010, 132, 8885-8887
10. Hartmann, M.; Li, Y.; Studer, A. J. Am. Chem. Soc. 2012, 134, 16516-16519
11. Su, Y.; Sun, X.; Wu, G.; Jiao, N. Angew. Chem., Int. Ed. 2013, 52, 9808-9812
12. Toh, K. K.; Sanjaya, S.; Sahnoun, S.; Chong, S. Y.; Chiba, S. Org. Lett. 2012, 14, 2290-2292
13. Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2011, 13, 3076-3079
14. Yanagihara, N.; Lambert, C.; Iritani, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 2753-2754
15. Luo, F.-T.; Schreuder, I.; Wang, R.-T. J. Org. Chem. 1992, 57, 2213-2215
16. Suero, M. G.; Bayle, E. D.; Collins, B. S. L.; Gaunt, M. J. J. Am. Chem. Soc. 2013, 135, 5332-5335
17. Cuenca, A. B.; Montserrat, S.; Hossain, K. M.; Mancha, G.; Lledós, A.; Medio-Simón, M.; Ujaque, G.; Asensio, G. Org. Lett. 2009, 11, 4906-4909
18. Xu, Z.-F.; Cai, C.-X.; Liu, J.-T. Org. Lett. 2013, 15, 2096-2099
19. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12-21
20. Ma, S. Acc. Chem. Res. 2003, 36, 701-712
21. For a recent review on preparation of allylic alcohols, see: Lumbroso, A.; Cooke, M. L.; Breit, B. Angew. Chem., Int. Ed. 2013, 52, 1890-1932
22. Husinec, S.; Petkovic, M.; Savic, V.; Simic, M. Synthesis 2012, 399-408
23. Husinec, S.; Jadranin, M.; Markovic, R.; Petkovic, M.; Savic, V.; Todorovic, N. Tetrahedron Lett. 2010, 51, 4066-4068
24. Chen, S.; Gao, Z.; Zhao, H.; Li, B. J. Org. Chem. 2014, 79, 1481-1486
25. Kawai, J.; Chikkade, P. K.; Shimizu, Y.; Kanai, M. Angew. Chem., Int. Ed. 2013, 52, 7177-7180
26. Chikkade, P. K.; Shimizu, Y.; Kanai, M. Chem. Sci. 2014, 5, 1585-1590
27. Han, S. B.; Kim, I. S.; Han, H.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 6916-6917
28. Hopkins, C. D.; Malinakova, H. C. Org. Lett. 2004, 6, 2221-2224
29. Meng, F.; Jang, H.; Jung, B.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2013, 52, 5046-5051
30. Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed. 2010, 49, 8181-8184
31. Boger, D. L.; Garbaccio, R. M.; Jin, Q. J. Org. Chem. 1997, 62, 8875-8891
32. Inokuchi, T.; Kawafuchi, H. Tetrahedron Lett. 2004, 60, 11969-11975
33. If aryl radical species were involved, cyclization to dihydrobenzofuran 9 should have been faster than intermolecular addition to allenes. See: Lockner, J. W.; Dixon, D. D.; Risgaard, R.; Baran, P. S. Org. Lett. 2011, 13, 5628-5631
34. Paderes, M. C.; Belding, L.; Fanovic, B.; Dudding, T.; Keister, J. B.; Chemler, S. R. Chem.-Eur. J. 2012, 18, 1711-1726