Regio- and stereoselective multisubstituted enol ester synthesis

Journal of Organic Chemistry

Volumn 76, Issue 21, 2011, Pages 9133-9138

  Okamoto, Noriko ^a,b   Miwa, Yoshihisa ^a   Minami, Hideki ^a   Takeda, Kei ^b   Yanada, Reiko ^a  

^a HIROSHIMA INTERNATIONAL UNIVERSITY   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLINGS; ENOL ESTERS; ONE POT PROCESS; STEREO-SELECTIVE;

ACETYLENE; ESTERIFICATION; ESTERS; OLEFINS;

STEREOSELECTIVITY;

ALKENE DERIVATIVE; ALKYNE; ESTER DERIVATIVE;

ARTICLE; COHALOGENATION; CROSS COUPLING REACTION; HALOGENATION; ONE POT SYNTHESIS; STEREOCHEMISTRY; SYNTHESIS;

ALCOHOLS; ALKENES; ALKYNES; ESTERS; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 80055076599     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201609r     Document Type: Article

References (51)

1. Reiser, O. Angew. Chem., Int. Ed. 2006, 45, 2838-2840
2. Itami, K.; Yoshida, J. Bull. Chem. Soc. Jpn. 2006, 79, 811-824
3. Mori, M. Eur. J. Org. Chem. 2007, 4981-4993
4. Flynn, A. B.; Ogilvie, W. W. Chem. Rev. 2007, 107, 4698-4745
5. Negishi, E.; Huang, Z.; Wang, G.; Mohan, S.; Wang, C.; Hattori, H. Acc. Chem. Res. 2008, 41, 1474-1485
6. Takahashi, A.; Kirio, Y.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1989, 111, 643-647 and references cited therein
7. Hansen, D. W., Jr. ; Pappo, R.; Garland, R. B. J. Org. Chem. 1988, 53, 4244-4253
8. Duan, H.; Sun, X.; Liao, W.; Petersen, J. L.; Shi, X. Org. Lett. 2008, 10, 4113-4116
9. Boaz, N. W. Tetrahedron Lett. 1998, 39, 5505-5508
10. Tang, W.; Liu, D.; Zhang., X. Org. Lett. 2003, 5, 205-207
11. Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 15044-15045
12. Trost, B. M.; Xu, J. J. Am. Chem. Soc. 2005, 127, 17180-17181
13. Rodoriguez, J.; Dulcère, J.-P. Synthesis 1993, 1177-1205
14. Stavber, S.; Jareb, M.; Zupan, M. Synthesis 2008, 1487-1513
15. Schreiber, S. L. Science 2000, 287, 1964-1969
16. Arya, P.; Chou, D. T. H.; Baek, M.-G. Angew. Chem., Int. Ed. 2001, 40, 339-346
17. Burke, M. D.; Berger, E. M.; Schreiber, S. L. Science 2003, 302, 613-618
18. Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46-58
19. Dowle, M. D.; Davies, D. I. Chem. Soc. Rev. 1979, 8, 171-197
20. Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321-3408
21. Robin, S.; Rousseau, G. Tetrahedron 1998, 54, 13681-13736
22. Barluenga, J.; Rodríguez, M. A.; Campos, P. J. J. Org. Chem. 1990, 55, 3104-3106
23. Barluenga, J.; Llorente, I.; Alvarez-García, L. J.; González, J. M.; Campos, P. J.; Díaz, M. R.; García-Granda, S. J. Am. Chem. Soc. 1997, 119, 6933-6934
24. Hénaff, N.; Whiting, A. J. Chem. Soc., Perkin Trans. 1 2000, 395-400
25. Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292-10296
26. Verma, A. K.; Joshi, M.; Singh, V. P. Org. Lett. 2011, 13, 1630-1633 and references cited therein
27. Olah, G. A.; Wang, Q.; Sandford, G.; Prakash, G. K. S. J. Org. Chem. 1993, 58, 3194-3195
28. Bovonsombat, P.; McNelis, E. Tetrahedron Lett. 1993, 34, 8205-8208
29. Castanet, A.-S.; Colobert, F.; Broutin, P.-E. Tetrahedron Lett. 2002, 43, 5047-5048
30. Prakash, G. K. S.; Mathew, T.; Hoole, D.; Esteves, P. M.; Wang, Q.; Rasul, G.; Olah, G. A. J. Am. Chem. Soc. 2004, 126, 15770-15776
31. Bovonsombat, P.; Leykajarakul, J.; Khan, C.; Pla-on, K.; Krause, M. M.; Khanthapura, P.; Ali, R.; Doowa, N. Tetrahedron Lett. 2009, 50, 2664-2667
32. CCDC 831998 (2l), CCDC 831999 (2m), CCDC 832000 (2n), and CCDC 832001 (2o) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
33. Pincock, J. A.; Yates, K. J. Am. Chem. Soc. 1968, 90, 5643-5644
34. Schmid, G. H.; Modro, A.; Yates., K. J. Org. Chem. 1980, 45, 665-667
35. Yates, K.; Go, T. A. J. Org. Chem. 1980, 45, 2377-2384
36. Bianchini, R.; Chiappe, C.; Lo Moro, G.; Lenoir, D.; Lemmen, P.; Goldberg, N. Chem. Eur. J. 1999, 5, 1570-1580
37. Okazaki, T.; Laali, K. K. J. Org. Chem. 2005, 70, 9139-9146
38. Okazaki, T.; Laali, K. K. J. Org. Chem. 2006, 71, 9643-9650
39. Lu, B.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 14070-14072
40. Lin, C.-H.; Wang, Y.-J.; Lee, C.-F. Eur. J. Org. Chem. 2010, 4368-4371
41. Chen, M.; Zheng, X.; Li, W.; He, J.; Lei, A. J. Am. Chem. Soc. 2010, 132, 4101-4103
42. Zhang, X.; Larock, R. C. Org. Lett. 2003, 5, 2993-2996
43. Roesch, K. R.; Larock, R. C. J. Org. Chem. 2001, 66, 412-420
44. Molander, G. A.; Katona, B. W.; Machrouhi, F. J. Org. Chem. 2002, 67, 8416-8423
45. Rao, M. L. N.; Jadhav, D. N.; Dasgupta, P. Org. Lett. 2010, 12, 2048-2051
46. Severin, R.; Reimer, J.; Doye, S. J. Org. Chem. 2010, 75, 3518-3521
47. Tsuchiya, K.; Chang, S.; W; Felix, N. M.; Ueda, M.; Ober, C. K. J. Photopolym. Sci. Technol. 2005, 18, 431-434
48. Okitsu, T.; Nakazawa, D.; Taniguchi, R.; Wada, A. Org. Lett. 2008, 10, 4967-4970
49. Kadnikov, D. V.; Larock, R. C. J. Org. Chem. 2004, 69, 6772-6780
50. Kotha, S.; Shah, V. R. E. J. Org. Chem. 2008, 1054-1064
51. Honzawa, S.; Hirasaka, K.; Yamamoto, Y.; Peleg, S.; Fujishima, T.; Kurihara, M.; Saito, N.; Kishimoto, S.; Sugiura, T.; Waku, K.; Takayama, H.; Kittaka, A. Tetrahedron 2005, 61, 11253-11263