Enantioselective intramolecular formal [2 + 4] annulation of acrylates and α,β-unsaturated imines catalyzed by amino acid derived phosphines

Organic Letters

Volumn 14, Issue 12, 2012, Pages 3226-3229

  Jin, Zhichao ^a   Yang, Ruojie ^a   Du, Yu ^a   Tiwari, Bhoopendra ^a   Ganguly, Rakesh ^a   Chi, Yonggui Robin ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMINO ACID; IMINE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ACRYLATES; AMINO ACIDS; CATALYSIS; IMINES; MOLECULAR STRUCTURE; PHOSPHINES; STEREOISOMERISM;

EID: 84862580047     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3013588     Document Type: Article

References (73)

1. Yet, L. Chem. Rev. 2000, 100, 2963
2. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
3. Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395
4. Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357
5. Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron Lett. 1997, 38, 4351
6. Kobayashi, S. Pure Appl. Chem. 1998, 70, 1019
7. Otto, S.; Engberts, J. B. F. N. Pure Appl. Chem. 2000, 72, 1365
8. Pellissier, H. Tetrahedron 2009, 65, 2839
9. Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2010, 33, 325
10. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471
11. Erkkilä, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416
12. MacMillan, D. W. C. Nature 2008, 455, 304
13. Han, B.; Li, J.-L.; Ma, C.; Zhang, S.-J.; Chen, Y.-C. Angew. Chem., Int. Ed. 2008, 47, 9971
14. Han, B.; He, Z.-Q.; Li, J. -L.; Li, R.; Jiang, K.; Liu, T.-Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2009, 48, 5474
15. Li, J.-L.; Kang, T.-R.; Zhou, S.-L.; Li, R.; Wu, L.; Chen, Y.-C. Angew. Chem., Int. Ed. 2010, 49, 6418
16. Jacobsen, E. N.; MacMillan, D. W. C. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20618
17. Jensen, K. L.; Dickmeiss, G.; Jiang, H.; Albrecht, L.; Jørgensen, K. A. Acc. Chem. Res. 2012, 45, 248
18. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535
19. Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035
20. Ye, L.-Wu; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140
21. Kwong, C. K.-W.; Fu, M. Y.; Lam, C. S.-L.; Toy, P. H. Synthesis 2008, 2307
22. Marinetti, A.; Voituriez, A. Synlett 2010, 174
23. Wei, Y.; Shi, M. Acc. Chem. Res. 2010, 43, 1005
24. Wang, S.; Han, X.; Zhong, F.; Wang, Y.; Lu, Y. Synlett 2011, 2766
25. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534
26. Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130
27. Moore, J. L.; Rovis, T. Top. Curr. Chem. 2010, 291, 77
28. Chiang, P. C.; Bode, J. W. TCI Mail 2011, 149, 2
29. Biju, A. T.; Kuhl, N.; Glorius, F. Acc. Chem. Res. 2011, 44, 1182
30. Cohen, D. T.; Scheidt, K. A. Chem. Sci. 2012, 3, 53
31. Rauhut, M. M.; Currier, H. (American Cyanamid Co.) U.S. Patent 307,499,919,630,122, 1963; Chem. Abstr. 1963, 58, 11224a. For reviews and examples of the Rauhut-Currier reactions, see
32. Aroyan, C. E.; Dermenci, A.; Miller, S. J. Tetrahedron 2009, 65, 4069 and references cited therein
33. Lu's pioneering work: Zhang, F. C.; Lu, X. J. Org. Chem. 1995, 60, 2906
34. Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836
35. Cowen, B. J.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 10988
36. Fang, Y. Q.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 5660
37. Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1426
38. Voituriez, A.; Panossian, A.; Fleury-Bregeot, N.; Retailleau, P.; Marinetti, A. J. Am. Chem. Soc. 2008, 130, 14030
39. Xiao, H.; Chai, Z.; Zheng, C.-W.; Yang, Y.-Q.; Liu, W.; Zhang, J.-K.; Zhao, G. Angew. Chem., Int. Ed. 2010, 49, 4467
40. Fujiwara, Y.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 12293
41. Han, X.; Wang, S.-X.; Zhong, F.; Lu, Y. Synthesis 2011, 1859
42. Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2011, 50, 7837
43. Tan, B.; Candeias, N. R.; Barbas, C. F., III. J. Am. Chem. Soc. 2011, 133, 4672
44. Han, X.; Wang, Y.; Zhong, F.; Lu, Y. J. Am. Chem. Soc. 2011, 133, 1726
45. Zhao, Q.-Y.; Han, X.; Wei, Y.; Shi, M.; Lu, Y. Chem. Commun. 2012, 48, 970
46. Han, X.; Zhong, F.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2012, 51, 767
47. Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716
48. Wurz, R. P.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 12234
49. Tran, Y. S.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 12632
50. Guo, H.; Xu, Q.; Kwon, O. J. Am. Chem. Soc. 2009, 131, 6318
51. Wang, T.; Ye, S. Org. Lett. 2010, 12, 4168
52. Tran, Y. S.; Martin, T. J.; Kwon, O. Chem.-Asian J. 2011, 6, 2101
53. Xiao, H.; Chai, Z.; Wang, H.-F.; Wang, X.-W.; Cao, D.-D.; Liu, W.; Lu, Y.-P.; Yang, Y.-Q.; Zhao, G. Chem.-Eur. J. 2011, 11, 10562
54. Na, R.; Jing, C.; Xu, Q.; Jiang, H.; Wu, X.; Shi, J.; Zhong, J.; Wang, M.; Benitez, D.; Tkatchouk, E.; Goddard, W. A., III; Guo, H.; Kwon, O. J. Am. Chem. Soc. 2011, 133, 13337
55. Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Chem. Sci. 2012, 3, 1231
56. Waldmann, H.; Khedhar, V.; Duckert, H.; Schurmann, M.; Oppel, I. M.; Kumar, K. Angew. Chem., Int. Ed. 2008, 47, 6869
57. Duckert, H.; Khedkar, V.; Waldmann, H.; Kumar, K. Chem.-Eur. J. 2011, 17, 5130
58. Sampath, M.; Loh, T.-P. Chem. Sci. 2010, 1, 739
59. During the preparation of this manuscript, Sasai et al. reported an excellent chiral phosphine-catalyzed enantioselective intramolecular Rauhut-Currier reaction of electron-deficient alkenes; see: Takizawa, S.; Nguyen, T. M.-N.; Grossmann, A.; Enders, D.; Sasai, H. Angew. Chem., Int. Ed. 2012, 51, 5423
60. He, L.; Jian, T.-Y.; Ye, S. J. Org. Chem. 2007, 72, 7466
61. He, L.; Zhang, Y.-R.; Huang, X.-L.; Ye, S. Synthesis 2008, 2825
62. Fang, X.; Jiang, K.; Xing, C.; Hao, L.; Chi, Y. R. Angew. Chem., Int. Ed. 2011, 50, 1910
63. Fang, X.; Chen, X.; Chi, Y. R. Org. Lett. 2011, 13, 4708
64. Fang, X.; Chen, X.; Lv, H.; Chi, Y. R. Angew. Chem., Int. Ed. 2011, 50, 11782
65. Hao, L.; Du, Y.; Lv, H.; Chen, X.; Jiang, H.; Shao, Y.; Chi, Y. R. Org. Lett. 2012, 14, 2154
66. Gong, J.; Li, T.; Pan, K.; Wu, X. Chem. Commun. 2011, 47, 1491
67. Zhong, F.; Wang, Y.; Han, X.; Huang, K.-W.; Lu, Y. Org. Lett. 2011, 13, 1310
68. Han, X.; Wang, Y.; Zhong, F.; Lu, Y. Org. Biomol. Chem. 2011, 9, 6734
69. Song, H.; Yuan, K.; Wu, X. Chem. Commun. 2011, 47, 1012
70. Saito, T.; Kimura, H.; Sakamaki, K.; Karakasa, T.; Moriyama, S. Chem. Commun. 1996, 811
71. Kobayashi, S.; Furuya, T.; Otani, T.; Saito, T. Tetrahedron 2008, 64, 9705
72. Kobayashi, S.; Semabs, T.; Takahashi, T.; Yoshida, S.; Dai, K.; Otani, T.; Saito, T. Tetrahedron 2009, 65, 920
73. Li, J.-L.; Zhou, S.-L.; Han, B.; Wu, L.; Chen, Y.-C. Chem. Commun. 2010, 46, 2665