Relaying asymmetry of transient atropisomers of o-iodoanilides by radical cyclizations

Journal of the American Chemical Society

Volumn 127, Issue 43, 2005, Pages 14994-14995

  Petit, Marc ^a   Lapierre, Andre J B ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 IODOANILIDE DERIVATIVE; ANILIDE; ISOMERASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATIONAL TRANSITION; CYCLIZATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 27544499159     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055666d     Document Type: Article

References (21)

1. (a) Zhao, H.; Hsu, D. C.; Carlier, P. R. Synthesis 2005, 1-16.
2. (b) Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373-376.
3. (a) Dalgard, J. E.; Rychnovsky, S. D. Org Lett 2004, 6, 2713-2716.
4. (b) Rychnovsky, S. D.; Hata, T.; Kim, A. I.; Buckmelter, A. I.; Org. Lett. 2001, 3, 807-810.
5. (c) Buckmelter, A. J.; Kim, A. I.; Rychnovsky, S. D. J. Am. Chem. Soc. 2000, 122, 9386-9390.
6. (d) Buckmelter, A. J.; Powers, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 1998, 120, 5589-5590.
7. (a) Giese, B.; Wettstein, P.; Stahelin, C.; Barbosa, F.; Neuburger, M.; Zehnder, M.; Wessig, P. Angew. Chem., Int. Ed. 1999, 38, 2586-2587.
8. (b) Seiler, M.; Schumacher, A.; Lindemann, U.; Barbosa, F.; Giese, B. Synlett 1999, 1588-1590.
9. (c) Sinicropi, A.; Barbosa, F.; Basosi, R.; Giese, B.; Olivucci, M. Angew. Chem., Int. Ed. 2005, 44, 2390-2393.
10. (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: Weinheim, 1996; Chapter 2.
11. (b) Porter, N. A. In Radicals in Organic Synthesis, 1st ed.; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, pp 416-440.
12. Jones, K.; McCarthy, C. Tetrahedron Lett. 1989, 30, 2657-2660.
13. (a) Curran, D. P.; Liu, W. D.; Chen, C. H.-T. J. Am. Chem. Soc. 1999, 121, 11012-11013.
14. (b) Ates, A.; Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131.
15. (c) Curran, D. P.; Chen, C. H.-T.; Geib, S. J.; Lapierre, A. J. B. Tetrahedron 2004, 60, 4413-4424.
16. (d) Petit, M.; Geib, S. J.; Curran, D. P. Tetrahedron 2004, 60, 7543-7552.
17. Assignments of configuration are presented in the Supporting Information.
18. (a) Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131-3132.
19. (b) Curran, D. P.; Geib, S.; DeMello, N. Tetrahedron 1999, 55, 5681-5704.
20. (c) During the publication process of this paper, resolutions of two o-iodoanilides were reported: Adler, T.; Bonjoch, J.; Clayden, J.; Font-Bardía, M.; Pickworth, M. Solans, X., Sole, D. Vallverdú, Org. Biomol. Chem. 2005, 3, 3173-3183.
21. Control experiments at partial conversion showed that (M,S)-5 and (P,S)-5 were consumed at about equal rates, so diastereoselective iodine abstraction seems unlikely.