Diastereo- and enantioselective propargylation of benzofuranones catalyzed by pybox-copper complex

Organic Letters

Volumn 16, Issue 21, 2014, Pages 5584-5587

  Zhao, Long ^a   Huang, Guanxin ^a   Guo, Beibei ^a   Xu, Lijun ^b   Chen, Jie ^a   Cao, Weiguo ^a   Zhao, Gang ^b   Wu, Xiaoyu ^a  

^a SHANGHAI UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BENZOFURAN DERIVATIVE; COPPER; KETONE; PARGYLINE;

ANALOGS AND DERIVATIVES; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYNES; BENZOFURANS; CATALYSIS; COPPER; KETONES; MOLECULAR STRUCTURE; PARGYLINE; STEREOISOMERISM;

EID: 84910020188     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502615y     Document Type: Article

References (47)

1. Oxford, A. E.; Raistrick, H.; Simonart, P. Biochem. J. 1939, 33, 240-248
2. Davies, R. R. Antifungal Chemotherapy; Wiley & Sons: New York, 1980; p 149.
3. Proksch, P.; Edrada, R.; Ebel, R.; Bohnenstengel, F. I.; Nugroho, B. W. Curr. Org. Chem. 2001, 5, 923-938 and references therein
4. Davey, A. E.; Schaeffer, M. J.; Taylor, R. J. K. J. Chem. Soc., Chem. Commun. 1991, 1137-1139
5. Davey, A. E.; Schaeffer, M. J.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1992, 2657-2666
6. Dobler, M. R.; Bruce, I.; Cederbaum, F.; Cooke, N. G.; Diorazio, L. J.; Hall, R. G.; Irving, E. Tetrahedron Lett. 2001, 42, 8281-8284
7. Diedrichs, N.; Ragot, J. P.; Thede, K. Eur. J. Org. Chem. 2005, 1731-1735
8. Li, H. S.; Fu, B.; Wang, M. A.; Li, N.; Liu, W. J.; Xie, Z. Q.; Ma, Y. Q.; Qin, Z. H. Eur. J. Org. Chem. 2008, 1753-1758
9. Thuaud, F.; Bernard, Y.; Turkeri, G.; Dirr, R.; Aubert, G.; Cresteil, T.; Baguet, A.; Tomasetto, G.; Svitkin, Y.; Sonenberg, N.; Nebigil, C. G.; Désaubry, L. J. Med. Chem. 2009, 52, 5176-5187
10. Ribeiro, N.; Thuaud, F.; Bernard, Y.; Gaiddon, C.; Cresteil, T.; Hild, A.; Hirsch, E. C.; Nebigil, C. G.; Désaubry, L. J. Med. Chem. 2012, 55, 10064-10073
11. For a review, see: Li, Y.; Li, X.; Cheng, J. P. Adv. Synth. Catal. 2014, 356, 1172-1198
12. Pirrung, M. C.; Brown, W. L.; Rege, S.; Laughton, P. J. Am. Chem. Soc. 1991, 113, 8561-8562
13. Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729
14. Nakajima, M.; Yamamoto, S.; Yamaguchi, Y.; Nakamura, S.; Hashimoto, S. Tetrahedron 2003, 59, 7307-7313
15. Wang, Y.; Liu, X. F.; Deng, L. J. Am. Chem. Soc. 2006, 128, 3928-3930
16. Ogawa, C.; Kizu, K.; Shimizu, H.; Takeuchi, M.; Kobayashi, S. Chem. - Asian. J. 2006, 1, 121-124
17. Capuzzi, M.; Perdicchia, D.; Jørgensen, K. A. Chem. - Eur. J. 2008, 14, 128-135
18. Akiyama, T.; Katoh, T.; Mori, K. Angew. Chem., Int. Ed. 2009, 48, 4226-4228
19. Wang, X. S.; Lan, Q.; Shirakawa, S.; Maruoka, K. Chem. Commun. 2010, 46, 321-323
20. Dong, N.; Li, X.; Wang, F.; Cheng, J. P. Org. Lett. 2013, 15, 4896-4899
21. Imada, Y.; Yuasa, M.; Nakamura, I.; Murahashi, S.-I. J. Org. Chem. 1994, 59, 2282-2284
22. Ljungdahl, N.; Kann, N. Angew. Chem., Int. Ed. 2009, 48, 642-644
23. Ding, C.-H.; Hou, X.-L. Chem. Rev. 2011, 111, 1914-1937
24. Detz, R. J.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2009, 6263-6276
25. Debleds, O.; Gayon, E.; Vrancken, E.; Campagne, J.-M. Beilstein J. Org. Chem. 2011, 7, 866-877
26. Nishibayashi, Y. Synthesis 2012, 44, 489-503
27. Inada, Y.; Nishibayashi, Y.; Uemura, S. Angew. Chem., Int. Ed. 2005, 44, 7715-7717
28. Matsuzawa, H.; Kanao, K.; Miyake, Y.; Nishibayashi, Y. Org. Lett. 2007, 9, 5561-5564
29. Matsuzawa, H.; Miyake, Y.; Nishibayashi, Y. Angew. Chem., Int. Ed. 2007, 46, 6488-6491
30. Fukamizu, K.; Miyake, Y.; Nishibayashi, Y. J. Am. Chem. Soc. 2008, 130, 10498-10499
31. Ikeda, M.; Miyake, Y.; Nishibayashi, Y. Angew. Chem., Int. Ed. 2010, 49, 7289-7293
32. Ikeda, M.; Miyake, Y.; Nishibayashi, Y. Chem. - Eur. J. 2012, 18, 3321-3328
33. Detz, R. J.; Delville, M. M. E.; Hiemstra, H.; van Maarseveen, J. H. Angew. Chem., Int. Ed. 2008, 47, 3777-3780
34. Detz, R. J.; Abiri, Z.; le Griel, R.; Hiemstra, H.; van Maarseveen, J. H. Chem. - Eur. J. 2011, 17, 5921-5930
35. Hattori, G.; Matsuzawa, H.; Miyake, Y.; Nishibayashi, Y. Angew. Chem., Int. Ed. 2008, 47, 3781-3783
36. Shibata, M.; Nakajima, K.; Nishibayashi, Y. Chem. Commun. 2014, 50, 7874-7877
37. Hattori, G.; Sakata, K.; Matsuzawa, H.; Tanabe, Y.; Miyake, Y.; Nishibayashi, Y. J. Am. Chem. Soc. 2010, 132, 10592
38. Fang, P.; Hou, X. L. Org. Lett. 2009, 11, 4612-4615
39. Zhang, C.; Hu, X. H.; Wang, Y. H.; Zheng, Z.; Xu, J.; Hu, X. P. J. Am. Chem. Soc. 2012, 134, 9585-9588
40. Zhu, F. L.; Zou, Y.; Zhang, D. Y.; Wang, Y. H.; Hu, X. H.; Chen, S.; Xu, J.; Hu, X. P. Angew. Chem., Int. Ed. 2014, 53, 1410-1414
41. Han, F. Z.; Zhu, F. L.; Wang, Y. H.; Zou, Y.; Hu, X. H.; Chen, S.; Hu, X. P. Org. Lett. 2014, 16, 588-591
42. Zhu, F. L.; Wang, Y. H.; Zhang, D. Y.; Hu, X. H.; Chen, S.; Hou, C. J.; Xu, J.; Hu, X. P. Adv. Synth. Catal. DOI: 10.1002/adsc.201400218.
43. Zhu, F. L.; Wang, Y. H.; Zhang, D. Y.; Xu, J.; Hu, X. P. Angew. Chem., Int. Ed. 2014, 53, 10223-10227
44. CCDC-1014538 (for 3a) and CCDC-1022280 (for 3ag) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
45. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210-216
46. Cao, T.; Linton, E. C.; Deitch, J.; Berritt, S.; Kozlowski, M. C. J. Org. Chem. 2012, 77, 11034-11055
47. Imagawa, H.; Takahiro Kurisaki, T.; Nishizawa, M. Org. Lett. 2004, 6, 3679-3681