Domino alkene-isomerization-Claisen rearrangement strategy to substituted allylsilanes

Journal of Organic Chemistry

Volumn 77, Issue 4, 2012, Pages 2058-2063

  McLaughlin, Mark G ^a   Cook, Matthew J ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLSILANES; CLAISEN REARRANGEMENT; DIASTEREOSELECTIVITIES; DIVINYL ETHER; ONE POT;

BUTADIENE; ETHERS; IRIDIUM; ISOMERIZATION; OLEFINS;

ISOMERS;

ALKENE; ALLYL COMPOUND; IRIDIUM; SILANE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CLAISEN REARRANGEMENT; DIASTEREOISOMER; ISOMERIZATION; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 84857215629     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202560g     Document Type: Article

References (40)

1. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293
2. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063
3. Chabaud, L.; James, P.; Landais, Y. Eur. J. Org. Chem. 2004, 3173
4. Schmidt, A. W.; Knolker, H.-J. Synlett 2010, 2207
5. Panek, J. S.; Cirillo, P. F. J. Org. Chem. 1993, 58, 999
6. Masse, C. E.; Dakin, L. A.; Knight, B. S.; Panek, J. S. J. Org. Chem. 1997, 62, 9335
7. Sun, P.; Sun, C.; Weinreb, S. M. J. Org. Chem. 2002, 67, 4337
8. Loreto, M. A.; Tardella, P. A.; Tofani, D. Tetrahedron Lett. 1995, 36, 8295
9. Beresis, R. T.; Masse, C. E.; Panek, J. S. J. Org. Chem. 1995, 60, 7714
10. Panek, J. S.; Beresis, R. T. J. Am. Chem. Soc. 1993, 115, 7898
11. Angle, S. D.; El-Said, N. A. J. Am. Chem. Soc. 2002, 124, 3608
12. Barbero, A.; Castrenõ, P.; Pulid, F. J. J. Am. Chem. Soc. 2005, 127, 8022
13. Dowling, M. S.; Vanderwal, C. D. J. Am. Chem. Soc. 2009, 131, 15090
14. Enders, D.; Lohray, B. B. Angew. Chem., Int. Ed. Engl. 1988, 27, 581
15. Arefolov, A.; Panek, J. S. J. Am. Chem. Soc. 2005, 127, 5595
16. Wrona, I. E.; Gozman, A.; Taldone, T.; Chiosis, G.; Panek, J. S. J. Org. Chem. 2010, 75, 2820
17. McLaughlin, M. G.; Cook, M. J. Chem. Commun. 2011, 47, 11104
18. Beresis, R. T.; Solomon, J. S.; Yang, M. G.; Jain, N. F.; Panek, J. S. Org. Synth. 1998, 75, 78
19. Beresis, R. T.; Solomon, J. S.; Yang, M. G.; Jain, N. F.; Panek, J. S. Organic Syntheses; Wiley: New York, 2004; Vol. 10, p 531.
20. Sparks, M. A.; Panek, J. S. J. Org. Chem. 1991, 56, 3431
21. Procter, G.; Russell, A. T.; Murphy, P. J.; Tan, T. S.; Mather, A. N. Tetrahedron 1988, 44, 3953
22. Murphy, P. J.; Spencer, J. L.; Procter, G. Tetrahedron Lett. 1990, 31, 1055
23. Panek, J. S.; Beresis, R.; Xu, F.; Yang, M. J. Org. Chem. 1991, 56, 7341
24. Fleming, I.; Hill, J. H. M.; Parker, D.; Waterson, D. J. Chem. Soc., Chem. Commun. 1985, 318
25. Sasaki, M.; Ikemoto, H.; Kawahata, M.; Yamaguchi, K.; Takeda, K. Chem.-Eur. J. 2009, 15, 4663
26. Majumdar, K. C.; Alam, S.; Chattopadhyay, B. Tetrahedron 2008, 64, 597
27. Mitchell, T. N.; Gieelmann, F. Synlett. 1996, 475
28. Schmidt, B. Synlett 2004, 1541
29. Higashino, T.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2000, 2, 4193
30. Ohumura, T.; Yamamoto, Y.; Miyaura, N. Organometallics 1998, 18, 413
31. Ohumura, T.; Yamamoto, Y.; Miyaura, N. Chem. Commun. 1998, 1337
32. Nelson, S. G.; Bungard, C. J.; Wang, K. J. Am. Chem. Soc. 2003, 125, 13000
33. Nelson, S. G.; Wang, K. J. Am. Chem. Soc. 2006, 128, 4232
34. Stevens, B. D.; Bungard, C. J.; Nelson, S. G J. Org. Chem. 2006, 71, 6397
35. Wang, K.; Bungard, C. J.; Nelson, S. G. J. Org. Lett. 2007, 9, 2325
36. Kerrigan, N. J.; Bungard, C. J.; Nelson, S. G. Tetrahedron 2008, 64, 6863
37. Hirsch, J. A. Top. Stereochem. 1967, 3, 199
38. Jensen, F. R.; Bushweller, C. H. Adv. Alicycl. Chem. 1971, 3, 139
39. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1993; p 696.
40. Eliel, E. L.; Wilen, S. H.; Doyle, M. P. Basic Organic Stereochemistry; Wiley: New York, 2001; p 443.