Asymmetric construction of spirocyclopentenebenzofuranone core structures via highly selective phosphine-catalyzed [3 + 2] cycloaddition reactions

Organic Letters

Volumn 15, Issue 12, 2013, Pages 2958-2961

  Albertshofer, Klaus ^a   Tan, Bin ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; STEREOISOMERISM;

BENZOFURANS; CATALYSIS; CYCLOADDITION REACTION; MOLECULAR STRUCTURE; PHOSPHINES; STEREOISOMERISM;

EID: 84879342812     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401087a     Document Type: Article

References (55)

1. Shen, Z.; Falshaw, C. P.; Haslam, E.; Begley, M. J. J. Chem. Soc., Chem. Commun. 1985, 1135
2. Piacente, S.; Montoro, P.; Oleszek, W.; Pizza, C. J. Nat. Prod. 2004, 67, 882
3. Wada, S.-I.; Hitomi, T.; Tanaka, R. Helv. Chim. Acta 2009, 92, 1610
4. Wada, T.; Hitomi, H.; Tokuda, R.; Tanaka Chem. Biodiversity 2010, 7, 2303
5. Onan, K. D.; Kelley, C. J.; Patarapanich, C.; Leary, J. D.; Aladesanmi, A. J. J. Chem. Soc., Chem. Commun. 1985, 121
6. Aladesanmi, A. J.; Adewunmi, C. O. Fitoterapia 1995, 66, 84
7. Trost, B. M.; Cramer, N.; Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396
8. Cassani, C.; Tian, X.; Escudero-Adan, E. C.; Melchiorre, P. Chem. Commun. (Cambridge, U.K.) 2011, 47, 233
9. Cao, Y.; Jiang, X.; Liu, L.; Shen, F.; Zhang, F.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 9124
10. Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580
11. Enders, D.; Grondal, C.; Huttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
12. Barbas, C. F., III. Angew. Chem., Int. Ed. 2008, 47, 42
13. Ramachary, D. B.; Kishor, M.; Reddy, Y. V. Eur. J. Org. Chem. 2008, 6, 975
14. Westemann, B.; Muhammad, A.; van Berkel, S. S. Angew. Chem., Int. Ed. 2010, 49, 846
15. Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430
16. Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836
17. Chen, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Org. Chem. 1998, 63, 5631
18. Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813
19. Shaw, S. A.; Aleman, P.; Vedejs, E. J. Am. Chem. Soc. 2003, 125, 13368
20. Shi, M.; Chen, L.-H.; Li, C.-Q. J. Am. Chem. Soc. 2005, 127, 3790
21. Wurz, R. P.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 12234
22. Marinetti, A.; Voituriez, A. Synlett 2010, 174
23. Fan, Y. C.; Kwon, O. Sci. Synth., Asymm. Organocatal. 2012, 1, 723
24. Cowen, B. J.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 10988
25. Voituriez, A.; Pinto, N.; Neel, M.; Retailleau, P.; Marinetti, A. Chem.-Eur. J. 2010, 16, 12541
26. Tan, B.; Candeias, N. R.; Barbas, C. F., III. J. Am. Chem. Soc. 2011, 133, 4672
27. Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2011, 50, 7837
28. Deng, H.-P.; Wei, Y.; Shi, M. Org. Lett. 2011, 13, 3348
29. Duvvuru, D.; Pinto, N.; Gomez, C.; Betzer, J.-F.; Retailleau, P.; Voituriez, A.; Marinetti, A. Adv. Synth. Catal. 2012, 354, 408
30. Tan, B.; Candeias, N. R.; Barbas, C. F., III. Nat. Chem. 2011, 3, 473
31. Tan, B.; Hernandez-Torres, G.; Barbas, C. F., III. J. Am. Chem. Soc. 2011, 133, 12354
32. Tan, B.; Zeng, X.; Leong, W. W. Y.; Shi, Z.; Barbas, C. F., III; Zhong, G. Chem.-Eur. J. 2012, 18, 63
33. Albertshofer, K.; Tan, B.; Barbas, C. F., III. Org. Lett. 2012, 14, 1834
34. Albertshofer, K.; Anderson, K.; Barbas, C. F., III. Org. Lett. 2012, 14, 5968
35. Wang, Q.-G.; Zhu, S.-F.; Ye, L.-W.; Zhou, C.-Y.; Sun, X.-L.; Tang, Y.; Zhou, Q.-L. Adv. Synth. Catal. 2010, 352, 1914
36. Hong, L.; Sun, W.; Liu, C.; Zhao, D.; Wang, R. Chem. Commun. (Cambridge, U.K.) 2010, 46, 2856
37. Wang, Q.-G.; Zhu, S.-F.; Ye, L.-W.; Zhou, C.-Y.; Sun, X.-L.; Tang, Y.; Zhou, Q.-L. Adv. Synth. Catal. 2010, 352, 1914
38. Yang, Y.-L.; Pei, C.-K.; Shi, M. Org. Biomol. Chem. 2011, 9, 3349
39. Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2011, 50, 7837
40. Deng, H.-P.; Wang, D.; Wei, Y.; Shi, M. Beilstein J. Org. Chem 2012, 8, 1098
41. Deng, H.-P.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2012, 354, 783
42. Hu, F.; Wei, Y.; Shi, M. Tetrahedron 2012, 68, 7911
43. Huang, X.; Peng, J.; Dong, L.; Chen, Y.-C. Chem. Commun. (Cambridge, U.K.) 2012, 48, 2439
44. Wang, D.; Yang, Y.-L.; Jiang, J.-J.; Shi, M. Org. Biomol. Chem. 2012, 10, 7158
45. Wang, Y.; Liu, L.; Zhang, T.; Zhong, N.-J.; Wang, D.; Chen, Y.-J. J. Org. Chem. 2012, 77, 4143
46. Zhang, X.-N.; Deng, H.-P.; Huang, L.; Wei, Y.; Shi, M. Chem. Commun. (Cambridge, U.K.) 2012, 48, 8664
47. Zhong, F.; Chen, G.-Y.; Han, X.; Yao, W.; Lu, Y. Org. Lett. 2012, 14, 3764
48. Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518
49. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125
50. Pilkington, C. J.; Zanotti-Gerosa, A. Org. Lett. 2003, 5, 1273
51. Kagan, H. B.; Dang, T. P. J. Chem. Soc. D 1971, 481
52. Kagan, H. B; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429
53. Zhang, X.; Tang, W. The Penn State Research Foundation, USA. Patent Application WO, 2003, 70 pp.
54. Zhang, X.; Tang, W. The Penn State Research Foundation, USA. Patent Application: US, 2004, 41 pp, Cont-in-part of US Ser. No. 291, 232.
55. Liu, D.; Zhang, X. Eur. J. Org. Chem. 2005, 646