Organocatalytic sequential Michael reactions: Stereoselective synthesis of multifunctionalized tetrahydroindan derivatives

Organic Letters

Volumn 13, Issue 5, 2011, Pages 936-939

  He, Peng ^a   Liu, Xiaohua ^a   Shi, Jian ^a   Lin, Lili ^a   Feng, Xiaoming ^a  

^a Sichuan University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CINCHONA ALKALOID; CYCLOPENTANE DERIVATIVE; INDAN DERIVATIVE; NITRO DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKENES; CATALYSIS; CINCHONA ALKALOIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOPENTANES; INDANS; MOLECULAR STRUCTURE; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 79952124258     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1029832     Document Type: Article

References (57)

1. Whelton, B. D.; Huitric, A. C. J. Org. Chem. 1971, 36, 1480
2. Aujard, I.; Röme, D.; Arzel, E.; Johansson, M.; Vos, D. D.; Sterner, O. Bioorg. Med. Chem. 2005, 13, 6145
3. Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P.; Magolda, R. L. J. Am. Chem. Soc. 1981, 103, 6969
4. Roege, K. E.; Kelly, W. L. Org. Lett. 2009, 11, 297
5. Sata, N. U.; Fusetani, N. Tetrahedron Lett. 2000, 41, 489
6. For selected examples, see: Benedetti, F.; Pitacco, G.; Valentin, E. Tetrahedron 1979, 35, 2293
7. Lin, Y. -T.; Houk, K. N. Tetrahedron Lett. 1985, 26, 2269
8. Richter, F.; Otto, H. H. Tetrahedron Lett. 1987, 28, 2945
9. Barco, A.; Benetti, S.; Risi, C. D.; Morelli, C. F.; Pollini, G. P.; Zanirato, V. Tetrahedron 1996, 52, 9275
10. Miao, S.; Anstee, M. R.; Baichwal, V.; Park, A. Tetrahedron Lett. 1995, 36, 5699
11. Shindo, K.; Sakakibara, M.; Kawai, H. J. Antibiot. 1996, 49, 249
12. Williams, D. R.; Brugel, T. A. Org. Lett. 2000, 2, 1023
13. Selkälä, S. A.; Koskinen, A. M. P. Eur. J. Org. Chem. 2005, 1620
14. Enders, D.; Hüttl, M. R. M.; Raabe, G.; Bats, J. W. Adv. Synth. Catal. 2008, 350, 267
15. McGarraugh, P. G.; Brenner, S. E. Org. Lett. 2009, 11, 5654
16. For reviews of the double Michael addition reaction, see: Grossman, R. B. Synlett. 2001, 13
17. Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. 1993, 32, 1010
18. For selected references to the synthesis of chiral cyclopentanes using α,β-unsaturated esters, see: Zu, L.; Xie, H.; Wang, J.; Tang, Y.; Wang, W. Angew. Chem., Int. Ed. 2007, 46, 3732
19. Tan, B.; Shi, Z.; Chua, P. J.; Zhong, G. Org. Lett. 2008, 10, 3425
20. For selected references to the synthesis of chiral cyclohexanone derivatives using γ,δ-unsaturated β-ketoesters and others, see: Thayumanavan, R.; Dhevalapally, B.; Sakthivel, K.; Tanaka, F.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 3817
21. Hoashi, Y.; Yabuta, T.; Takemoto, Y. Tetrahedron Lett. 2004, 45, 9185
22. Hoashi, Y.; Yabuta, T.; Yuan, P.; Miyabe, H.; Takemoto, Y. Tetrahedron 2006, 62, 365
23. Wu, L. -Y.; Bencivenni, G.; Mancinelli, M.; Mazzanti, A.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7196
24. For selected examples of constructed multistereocenters compounds, see: Tietze, L. F. Chem. Rev. 1996, 96, 115
25. Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636
26. Knopff, O.; Alexakis, A. Org. Lett. 2002, 4, 3835
27. Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272
28. Enders, D.; Hüttl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861
29. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134
30. Lu, M.; Zhu, D.; Lu, Y.; Hou, Y.; Tan, B.; Zhong, G. Angew. Chem., Int. Ed. 2008, 47, 10187
31. Zhu, D.; Lu, M.; Chua, P. J.; Tan, B.; Wang, F.; Yang, X.; Zhong, G. Org. Lett. 2008, 10, 4585
32. Tan, B.; Lu, Y.; Zeng, X.; Chua, P. J.; Zhong, G. Org. Lett. 2010, 12, 2682
33. Jiang, K.; Jia, Z.-J.; Yin, X.; Wu, L.; Chen, Y.-C. Org. Lett. 2010, 12, 2766
34. Ma, A.; Ma, D. Org. Lett. 2010, 12, 3634
35. Baslé, O.; Raimondi, W.; Duque, M. M. S.; Bonne, D.; Constantieux, T.; Rodriguez, J. Org. Lett. 2010, 12, 5246
36. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
37. Kraus, G. A.; Goronga, T. Synthesis 2007, 12, 1765
38. Palomo, C.; Oiarbide, M.; Laso, A. Eur. J. Org. Chem. 2007, 2561
39. For selected examples of chiral cinchona alkaloid organocatalysis, see: Chen, Y.; McDaid, P.; Deng, L. Chem. Rev. 2003, 103, 2965
40. Li, H.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906
41. Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2005, 44, 105
42. Li, H.; Wang, B.; Deng, L. J. Am. Chem. Soc. 2006, 128, 732
43. Wang, Y. -Q.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156
44. Wu, F.; Li, H.; Hong, R.; Deng, L. Angew. Chem., Int. Ed. 2006, 45, 947
45. Wu, F.; Hong, R.; Khan, J.; Liu, X.; Deng, L. Angew. Chem., Int. Ed. 2006, 45, 4301
46. Li, H.; Wang, Y. -Q.; Deng, L. Org. Lett. 2006, 8, 4063
47. Wang, Y.; Li, H.; Wang, Y. -Q.; Liu, Y.; Foxman, B. M.; Deng, L. J. Am. Chem. Soc. 2007, 129, 6364
48. Liu, T. -Y.; Cui, H. -L.; Chai, Q.; Long, J.; Li, B. J.; Wu, Y.; Ding, L. -S.; Chen, Y. -C. Chem. Commun. 2007, 2228
49. Hynes, P. S.; Stranges, D.; Stupple, P. A.; Guarna, A.; Dixon, D. J. Org. Lett. 2007, 9, 2107
50. Guo, C.; Xue, M. -X.; Zhu, M. -K.; Gong, L. -Z. Angew. Chem., Int. Ed. 2008, 47, 3414
51. Zhang, L.; Lee, M.-M.; Lee, S.-M.; Lee., J.; Cheng, M. S.; Jeong, B.-S.; Park, H.-G.; Jew, S.-S. Adv. Synth. Catal. 2009, 351, 3063
52. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Quim. Ind. 1979, 33, 1
53. Kornblum, N. Org. React. 1962, 12, 101
54. 2/petroleum ether = 1:10).
55. Yu, Z. P.; Liu, X. H.; Zhou, L.; Lin, L. L.; Feng, X. M. Angew. Chem., Int. Ed. 2009, 48, 5195
56. CCDC-803725 contains the supplementary crystallographic data of 3i. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
57. For details, see the Supporting Information.