Gold(I)-catalyzed synthesis of optically active 1,4-oxazepan-7-ones

Journal of Organic Chemistry

Volumn 79, Issue 16, 2014, Pages 7696-7702

  Kamimura, Akio ^a   Yamane, Yu ^a   Yo, Ryuichiro ^a   Tanaka, Toshiyuki ^a   Uno, Hidemitsu ^b  

^a YAMAGUCHI UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^b EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

CATALYTIC AMOUNTS; CATALYZED SYNTHESIS; OPTICALLY ACTIVE; TERT-BUTYL ESTERS;

ESTERS;

CARBOXYLIC ACID; GOLD; LACTONE DERIVATIVE; OXAZEPINE DERIVATIVE; ESTER; LACTONE; MESYLIC ACID DERIVATIVE; ORGANOMETALLIC COMPOUND; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYST; CONTROLLED STUDY; CYCLIZATION; DECOMPOSITION; DIASTEREOISOMER; HIGH TEMPERATURE; HYDROGENATION; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; CYCLIZATION; ESTERS; GOLD; LACTONES; MESYLATES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXAZEPINES; STEREOISOMERISM;

EID: 84906086175     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501254x     Document Type: Article

References (55)

1. Janot, M. M.; Goutarel, R.; Bosly, J. C. R. Hebd. Seances Acad. Sci. 1951, 232, 853
2. Bosley, J. J. Pharm. Belg. 1951, 6, 150
3. Cabenzas, F.; Arnoldo Ramírez, A.; Viladomat, F.; Codina, C.; Jaume Bastida, J. Chem. Pharm. Bull. 2003, 51, 315
4. For a review, see: Kurosu, M.; Kishi, Y. J. Synth. Org. Chem. Jpn. 2004, 62, 1205
5. Braekman, J.-C.; Charlier, A.; Daloze, D.; Heilporn, S.; Pasteels, J.; Plasman, V.; Wang, S. Eur. J. Org. Chem. 1999, 1749
6. Laurent, P.; Braekman, J.-C.; Daloze, D. Eur. J. Org. Chem. 2000, 2057
7. Rougnon-Glasson, S.; Tratrat, C.; Canet, J.-L.; Chalard, P.; Troin, Y. Tetrahedron: Asymmetry 2004, 15, 1561
8. Calvet-Vitale, S.; Vanucci-Bacqué, C.; Fargeau-Bellassoued, M.-C.; Lhommet, G. Tetrahedron 2005, 61, 7774
9. Kubiznaa, P.; Špánikb, I.; Kožíšek, J.; Szolcsányi, P. Tetrahedron 2010, 66, 2351
10. Rothman, R. B.; Katsnelson, M.; Vu, N.; Partilla, J. S.; Dersch, C. M.; Blough, B. E.; Baumann, M. H. Eur. J. Pharmacol. 2002, 447, 51
11. Rothman, R. B.; Baumann, M. H. Curr. Top. Med. Chem. 2006, 6, 1845
12. Zhou, L.; Tan, C. K.; Zhou, J.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 10245
13. Kamimura, A.; Okawa, H.; Morisaki, Y.; Ishikawa, S.; Uno, H. J. Org. Chem. 2007, 72, 3569
14. Ishikawa, S.; Noguchi, F.; Kamimura, A. J. Org. Chem. 2010, 75, 3578
15. Ishikawa, S.; Noguchi, F.; Uno, H.; Kamimura, A. Tetrahedron Lett. 2010, 51, 2329
16. Kamimura, A.; Ishikawa, S.; Noguchi, F.; Moriyama, T.; So, M.; Murafuji, T.; Uno, H. Chem. Commun. 2012, 48, 6592
17. Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657
18. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239
19. Corma, A.; Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180
20. Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410
21. Ma, S.; Yu, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200
22. Belmont, P.; Parker, E. Eur. J. Org. Chem. 2009, 6075
23. Rao, W.; Koh, M. J.; Li, D.; Hirao, H.; Chan, P. W. H. J. Am. Chem. Soc. 2013, 135, 7926
24. Gryparis, C.; Efe, C.; Raptis, C.; Lykakis, I. N.; Stratakis, M. Org. Lett. 2012, 14, 2956
25. Deschamps, N. M.; Elitzin, V. I.; Liu, B.; Mitchell, M. B.; Sharp, M. J.; Tabet, E. A. J. Org. Chem. 2011, 76, 712
26. Pradal, A.; Chao, C.-M.; Vitale, M. R.; Toullec, P. Y.; Michelet, V. Tetrahedron 2011, 67, 4371
27. Qiana, D.; Zhang, J. Chem. Commun. 2011, 47, 11152
28. Lemière, G.; Gandon, V.; Cariou, K.; Fukuyama, T.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2007, 9, 2207
29. Schelwies, M.; Dempwolff, A. L.; Rominger, F.; Helmchen, G. Angew. Chem., Int. Ed. 2007, 46, 5598
30. Lee, S. I.; Kim, S. M.; Choi, M. R.; Kim, S. Y.; Chung, Y. K. J. Org. Chem. 2006, 71, 9366
31. Obradors, C.; Echavarren, A. M. Acc. Chem. Res. 2014, 47, 902
32. Amijs, C. H. M.; López-Carrillo, V.; Raducan, M.; Pérez-Galán, P.; Ferrer, C.; Echavarren, A. M. J. Org. Chem. 2008, 73, 7721
33. Cabello, N.; Jiménez-Núñez, E.; Buñuel, E.; Cárdenas, D. J.; Echavarren, A. M. Eur. J. Org. Chem. 2007, 4217
34. López, S.; Herrero-Gómez, E.; Pérez-Galán, P.; Nieto-Oberhuber, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 6029
35. Nieto-Oberhuber, C.; Muñoz, M. P.; López, S.; Jiménez-Núñez, E.; Nevado, C.; Herrero-Gómez, E.; Raducan, M.; Echavarren, A. M. Chem. Eur. J. 2006, 12, 1677
36. Nieto-Oberhuber, C.; López, S.; Muñoz, M. P.; Jiménez-Núñez, E.; Buñuel, E.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2006, 12, 1694
37. Nieto-Oberhuber, C.; Muñoz, M. P.; Buæuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402
38. Harkat, H.; Dembelé, A. Y.; Weibel, J.-M.; Blanc, A.; Pale, P. Tetrahedron 2009, 65, 1871
39. Nguyen, K. H.; Tomasi, S.; Le Roch, M.; Toupet, L.; Renault, J.; Uriac, P.; Gouault, N. J. Org. Chem. 2013, 78, 7809
40. Shu, C.; Liu, M.-Q.; Wang, S.-S.; Li, L.; Ye, L.-W. J. Org. Chem. 2013, 78, 3292
41. Nguyen, K. H.; Tomasi, S.; Le Roch, M.; Toupet; Renault, J.; Uriac, P.; Gouault, N. J. Org. Chem. 2013, 78, 7809
42. Gregory, A. W.; Jakubec, P.; Turner, P.; Dixon, D. J. Org. Lett. 2013, 15, 4330
43. Hashmi, A. S. K.; Jaimes, M. C. B.; Schuster, A. M.; Rominger, F. J. Org. Chem. 2012, 77, 6394
44. Oh, C. H.; Lee, S. J.; Lee, J. H.; Na, Y. J. Chem. Commun. 2008, 5794
45. Buzas, A.; Gagosz, F. Org. Lett. 2006, 8, 515
46. Tomás-Mendivil, E.; Toullec, P. Y.; Díez, J.; Conejero, S.; Michelet, V.; Cadierno, V. Org. Lett. 2012, 14, 2520
47. Genin, E.; Toullec, P. Y.; Antoniotti, S.; Brancour, C.; Genêt, J.-P.; Michelet, V. J. Am. Chem. Soc. 2006, 128, 3112
48. Kang, J.-E.; Shin, S. Synlett 2006, 0717
49. Buzas, A.; Gagosz, F. Synlett 2006, 2727
50. Guérinot, A.; Fang, W.; Sircoglou, M.; Bour, C.; Bezzenine-Lafollée, S.; Gandon, V. Angew. Chem., Int. Ed. 2013, 52, 5848
51. Dang, T. T.; Boeck, F.; Hintermann, L. J. Org. Chem. 2011, 76, 9353
52. Kuo, Y.-H.; Chen, C.-H.; Chiang, Y.-M. Tetrahedron Lett. 2001, 42, 6731
53. Issa, H. H.; Tanaka, J.; Rachmat, R.; Higa, T. Tetrahedron Lett. 2003, 44, 1243
54. Briggs, T. F.; Dudley, G. B. Tetrahedron Lett. 2005, 46, 7793
55. Chen, Y.; Harmata, M. Tetrahedron Lett. 2011, 52, 4069