Radical and heck cyclizations of Diastereomeric o -haloanilide atropisomers

Journal of the American Chemical Society

Volumn 133, Issue 1, 2011, Pages 115-122

  Guthrie, David B ^a   Geib, Steven J ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMBIENT TEMPERATURES; ANTI ISOMERS; ATROPISOMERS; CYCLIZATIONS; DIASTEREOMERIC; DIASTEREOMERS; HECK REACTIONS; HYDRIDE ELIMINATION; INTERCONVERSIONS; METHYL GROUP; ORGANOMETALLIC INTERMEDIATES; RADICAL CYCLIZATIONS; STEREOCENTERS; SYN-ISOMERS;

FUNCTIONAL GROUPS; ISOMERS; ORGANOMETALLICS; PALLADIUM; TEMPERATURE;

CYCLIZATION;

ACETAMIDE DERIVATIVE; ACETIC ACID; ANILIDE; CARBAZOLE DERIVATIVE; METHYL GROUP; N (CYCLOHEX 2 ENYL) N (2 IODO 4,6 DIMETHYLPHENYL)ACETAMIDE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; ENVIRONMENTAL TEMPERATURE; HECK REACTION; ISOMER; RADICAL REACTION; REACTION ANALYSIS;

EID: 78650980643     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja108795x     Document Type: Article

References (34)

1. Curran, D. P., Liu, W. D., and Chen, C. H.-T. J. Am. Chem. Soc. 1999, 121, 11012-11013
2. Ates, A. and Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131
3. Petit, M., Geib, S. J., and Curran, D. P. Tetrahedron 2004, 60, 7543-7552
4. Jones, K. and McCarthy, C. Tetrahedron Lett. 1989, 30, 2657-2660
5. Petit, M., Lapierre, A. J. B., and Curran, D. P. J. Am. Chem. Soc. 2005, 127, 14994-14995
6. Curran, D. P., Chen, C. H. T., Geib, S. J., and Lapierre, A. J. B. Tetrahedron 2004, 60, 4413-4424
7. Guthrie, D. B. and Curran, D. P. Org. Lett. 2009, 11, 249-251
8. Lapierre, A. J. B., Geib, S. J., and Curran, D. P. J. Am. Chem. Soc. 2007, 129, 494-495
9. Alcaide, B., Almendros, P., Rodríguez-Vicente, A., and Ruiz, M. P. Tetrahedron 2005, 61, 2767-2778
10. Alcaide, B., Moreno, A. M., Rodríguez-Vicente, A., and Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203-2206
11. Lampard, C., Murphy, J. A., and Rasheed, F. Tetrahedron Lett. 1994, 35, 8675-8678
12. Kumar, R. R. and Kagan, H. B. Adv. Synth. Catal. 2010, 352, 231-242
13. Bruch, A., Ambrosius, A., Fröhlich, R., Studer, A., Guthrie, D. B., Zhang, H., and Curran, D. P. J. Am. Chem. Soc. 2010, 132, 11452-11454
14. The Mizoroki-Heck Reaction; Oestreich, M., Ed.; John Wiley & Sons: Chichester, U.K., 2009.
15. Gooflen, L. and Baumann, K. In Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005; pp 277 - 286.
16. Alonso, D. A. and Nájera, C. In Compounds with All-Carbon Functions. Alkenes; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 2009; Vol. 47a, pp 439 - 479.
17. Jutand, A. In The Mizoroki-Heck Reaction; Oestreich, M., Ed.; John Wiley & Sons: Chichester, U.K., 2009; pp 1 - 50.
18. Knowles, J. P. and Whiting, A. Org. Biomol. Chem. 2007, 5, 31-44
19. Curran, D. P., Porter, N. A., and Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: Weinheim, 1996; pp 51 - 71.
20. Adler, T., Bonjoch, J., Clayden, J., Font-Bardía, M., Pickworth, M., Solans, X., Solé, D., and Vallverdú, L. Org. Biomol. Chem. 2005, 3, 3173-3183
21. Johnston, L. J., Lusztyk, J., Wayner, D. D. M., Abeywickreyma, A. N., Beckwith, A. L. J., Scaiano, J. C., and Ingold, C. K. J. Am. Chem. Soc. 1985, 107, 4594-4596
22. Newcomb, M. Tetrahedron 1993, 49, 1151-1176
23. Jones, K. and Storey, J. M. D. J. Chem. Soc., Chem. Commun. 1992, 1766-1767
24. Lapierre, A. J. B. Ph.D. Dissertation, University of Pittsburgh, 2005.
25. Stambuli, J. P., Stauffer, S. R., Shaughnessy, K. H., and Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678
26. Beckwith, A. J. J. and Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941
27. Mori, M., Nakanishi, M., Kajishima, D., and Sato, Y. Org. Lett. 2001, 3, 1913-1916
28. Mori, M., Nakanishi, M., Kajishima, D., and Sato, Y. J. Am. Chem. Soc. 2003, 125, 9801-9807
29. Zhu, G. and Lu, X. Organometallics 1995, 14, 4899-4904
30. Mariampillai, B., Herse, C., and Lautens, M. Org. Lett. 2005, 7, 4745-4747
31. Lautens, M., Tayama, E., and Herse, C. J. Am. Chem. Soc. 2005, 127, 72-73
32. Similar selectivities in β-eliminations have been observed by Dr Christelle Herse of the University of Toronto as cited in the Thesis of Dr. Brian Mariampillai, University of Toronto, pp 158-159, 2009. We thank Prof. Mark Lautens for sharing this information.
33. Cheng, J. C.-Y., Daves, J., and Doyle, G. Organometallics 1986, 5, 1753-1755
34. Sinou, D. and Bedjeguelal, K. Eur. J. Org. Chem. 2000, 4071-4077