Highly enantiospecific platinum-catalyzed cycloisomerizations: Synthesis of enantioenriched oxabicycloheptene derivatives

Organic Letters

Volumn 15, Issue 7, 2013, Pages 1772-1775

  Newcomb, Eric T ^a   Ferreira, Eric M ^a  

^a Veterinary Dentistry and Oral Surgery   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84875934636     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400625f     Document Type: Article

References (48)

1. Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410-3449
2. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211
3. Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271-2296
4. Watson, I. D. G.; Toste, F. D. Chem. Sci. 2012, 3, 2899-2919
5. Marinetti, A.; Jullien, H.; Voituriez, A. Chem. Soc. Rev. 2012, 41, 4884-4908
6. Pradal, A.; Toullec, P. Y.; Michelet, V. Synthesis 2011, 1501-1514
7. Rooke, D. A.; Ferreira, E. M. J. Am. Chem. Soc. 2010, 132, 11926-11928
8. Allegretti, P. A.; Ferreira, E. M. Org. Lett. 2011, 13, 5924-5927
9. Allegretti, P. A.; Ferreira, E. M. Chem. Sci. 2013, 4, 1053-1058
10. Blum, J.; Beer-Kraft, H.; Badrieh, Y. J. Org. Chem. 1995, 60, 5567-5569
11. Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869
12. Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520
13. Ota, K.; Lee, S. I.; Tang, J.-M.; Takachi, M.; Nakai, H.; Morimoto, T.; Sakurai, H.; Kataoka, K.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 15203-15211
14. Shibata, T.; Kobayashi, Y.; Maekawa, S.; Toshida, N.; Takagi, K. Tetrahedron 2005, 61, 9018-9024
15. Chao, C.-M.; Beltrami, D.; Toullec, P. Y.; Michelet, V. Chem. Commun. 2009, 6988-6990
16. Brissy, D.; Skander, M.; Jullien, H.; Retailleau, P.; Marinetti, A. Org. Lett. 2009, 11, 2137-2139
17. Nishimura, T.; Kawamoto, T.; Nagaosa, M.; Kumamoto, H.; Hayashi, T. Angew. Chem., Int. Ed. 2010, 49, 1638-1641
18. Nishimura, T.; Maeda, Y.; Hayashi, T. Org. Lett. 2011, 13, 3674-3677
19. Teller, H.; Corbet, M.; Mantilli, L.; Gopakumar, G.; Goddard, R.; Thiel, W.; Fürstner, A. J. Am. Chem. Soc. 2012, 134, 15331-15342
20. Barbazanges, M.; Augé, M.; Moussa, J.; Amouri, H.; Aubert, C.; Desmarets, C.; Fensterbank, L.; Gandon, V.; Malacria, M.; Ollivier, C. Chem.-Eur. J. 2011, 17, 13789-13794
21. See the Supporting Information (SI) for related works.
22. He, R.-X.; Li, M.; Li, X.-Y. THEOCHEM 2005, 717, 21-32
23. Soriano, E.; Ballesteros, P.; Marco-Contelles, J. J. Org. Chem. 2004, 69, 8018-8023
24. Nevado, C.; Ferrer, C.; Echavarren, A. M. Org. Lett. 2004, 6, 3191-3194
25. Ferrer, C.; Raducan, M.; Nevado, C.; Claverie, C. K.; Echavarren, A. M. Tetrahedron 2007, 63, 6306-6316
26. Chen, Z.; Zhang, Y.-X.; Wang, Y.-H.; Zhu, L.-L.; Liu, H.; Li, X.-X.; Guo, L. Org. Lett. 2010, 12, 3468-3471
27. Xia, J.-B.; Liu, W.-B.; Wang, T.-M.; You, S.-L. Chem.-Eur. J. 2010, 22, 6442-6446
28. Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. 2006, 45, 2901-2904
29. Fürstner, A.; Hannen, P. Chem.-Eur. J. 2006, 12, 3006-3019
30. Fehr, C.; Winter, B.; Magpantay, I. Chem.-Eur. J. 2009, 15, 9773-9784
31. Fürstner, A.; Schlecker, A. Chem.-Eur. J. 2008, 14, 9181-9191
32. Soriano, E.; Marco-Contelles, J. J. Org. Chem. 2007, 72, 2651-2654
33. Gandon, Fensterbank, Malacria and coworkers have described an example of chirality transfer with propargylic ester substrates that first converts to a chiral allene intermediate. See: Gandon, V.; Lemière, G.; Hours, A.; Fensterbank, L.; Malacria, M. Angew. Chem., Int. Ed. 2008, 47, 7534-7538
34. Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757-824
35. Trost, B. M.; Weiss, A. H. Adv. Synth. Catal. 2009, 351, 963-983
36. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739
37. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102
38. Denmark, S. E.; Burk, M. T.; Hoover, A. J. J. Am. Chem. Soc. 2010, 132, 1232-1233
39. Greene, M. A.; Yonova, I. M.; Williams, F. J.; Jarvo, E. R. Org. Lett. 2012, 14, 4293-4296
40. Fürstner, A.; Davies, P. W.; Gress, T. J. Am. Chem. Soc. 2005, 127, 8244-8245
41. Nieto Faza, O.; de Lera, A. R. Top. Curr. Chem. 2011, 302, 81-130
42. Yu, W.; Mei, Y.; Kang, Y.; Hua, Z.; Jin, Z. Org. Lett. 2004, 6, 3217-3219
43. Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 899-970.
44. Davies, H. M. L. Tetrahedron 1993, 49, 5203-5223
45. Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198
46. Pellissier, H. Tetrahedron 2008, 64, 7041-7095
47. Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977-1050
48. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911-936