Stereoselection at the Steady State in Radical Cyclizations of Acyclic Systems Containing One Radical Acceptor and Two Precursors in a 1,5- Relationship under Pseudo-First-Order Conditions

Journal of Organic Chemistry

Volumn 69, Issue 6, 2004, Pages 1844-1848

  Andrukiewicz, Robert ^a   Cmoch, Piotr ^a   Gaweł, Anna ^a   Staliński, Krzysztof ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERS; REACTION KINETICS; SUBSTITUTION REACTIONS;

RADICAL CYCLIZATIONS; SUBSTITUENTS;

STEREOCHEMISTRY;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; GEOMETRY; KINETICS; STEADY STATE; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 1642309794     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035310p     Document Type: Article

References (39)

1. Lord, M. D.; Negri, J. T.; Paquette, L. A. J. Org. Chem. 1995, 60, 191-195.
2. (a) Shaw, D. E.; Fenton, G.; Knight, D. W. J. Chem. Soc., Chem. Commun. 1994, 2447-2448.
3. (b) Paolucci, C.; Mazzini, C.; Fava, A. J. Org. Chem. 1995, 60, 169-175.
4. Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819-10822.
5. Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 411-453.
6. (a) Lee, E.; Choi, S. J. Org. Lett. 1999, 7, 1127-1128.
7. (b) Lee, E.; Song, H. Y.; Kim, H. J. J. Chem. Soc., Perkin Trans. 1 1999, 3395-3396.
8. (c) Lee, E.; Jeong, E. J.; Kang, E. J.; Sung, L. T.; Hong, S. K. J. Am. Chem. Soc. 2001, 123, 10131-10132.
9. Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706-6716.
10. (a) Curran, D. P.; DeMello, N. C. J. Am. Chem. Soc. 1998, 120, 329-341.
11. (b) Curran, D. P.; DeMello, N. C.; Junggebauer, J.; Lin, C.-H. J. Am. Chem. Soc. 1998, 120, 342-351.
12. Kagan, H. Tetrahedron 2001, 47, 2449-2468.
13. (a) Curran, D. P.; Qi, H. Helv. Chim. Acta 1996, 79, 21-30.
14. (b) Curran, D. P.; Qi, H.; DeMello, N. C.; Lin, C.-H. J. Am. Chem. Soc. 1994, 116, 8430-8431.
15. (c) Villar, F.; Equey, O.; Renaud, P. Org. Lett. 2000, 2, 1061-1064.
16. (a) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959-974.
17. (b) Beckwith, A. L. J.; Lawrence, T.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482-483.
18. (c) Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 484-485.
19. Curran, D. P.; Staliński, K. J. Org. Chem. 2002, 67, 2982-2988.
20. Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213 and references therein.
21. (a) Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339-6348.
22. (b) Roush, W. R.; Ando, K.; Palkowitz, A. D. J. Am. Chem. Soc. 1990, 112, 6348-6359.
23. Compounds 10a,b are formed via a chairlike transition state. Compound 11 is presumably formed via a boatlike transition state.
24. -1; see: (a) Lusztyk, J.; Maillard, B.; Deycard, S.; Lindsay, D. A.; Ingold, K. U. J. Org. Chem. 1987, 52, 3509-3514.
25. (b) Beckwith, A. L. J.; Easton, C. J.; Lawrence, T.; Serelis, A. K. Aust. J. Chem. 1983, 36, 545-556.
26. (c) Chatgilialoglu, C.; Ferreri, C.; Lucarni, M. J. Org. Chem. 1991, 56, 6399-6403.
27. The products could not be separated by chromatography to give the individual pure isomers, Moreover, they appeared to be quite volatile, and we were not able to purify them from impurities, The phenyl groups in 2 allowed us to separate the reaction mixture by means of HPLC (UV detection) and added molecular weight so that the products were not volatile.
28. 1H NMR NOE enhancements in tetrahydrofurans are usually smaller than in other systems; see: Kadota, T.; Oguro, N.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 3645-3648.
29. Newcomb, M.; Homer, J. H.; Filipowski, M. A.; Ha, C.; Park, S,-U. J. Am. Chem. Soc, 1995, 117, 3674-3684.
30. 3SnH. But the analysis of small quantities of the products in the presence of a large excess of the hydride could be very difficult and give rather inconsistent results. Therefore, we then turned our attention to the use of much faster trapping agents.
31. Newcomb, M.; Varick, T. R.; Ha, Ch.; Manek, M. B.; Yue, X. J. Am. Chem. Soc. 1992, 114, 8158-8163.
32. Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986; p 26.
33. Crich, D.; Jiao, X.-Y.; Yao, Q.; Harwood, J. S. J. Org. Chem. 1996, 61, 2368-2373.
34. Franz, J. A.; Bushaw, B. A.; Alnajjar, M. S. J. Am. Chem. Soc. 1989, 111, 268-275.
35. 13a,b after being resubjected to the reaction conditions appeared to be stable and were recovered almost quantitatively (> 96%).
36. For comparison purposes 19 was prepared independently. Commercially available diisopropyl ketone was reduced with lithium aluminum hydride, and the resulting alcohol was reacted with an excess of 1,1-dimethoxy-2,2-diphenylacetaldehyde acetal in the presence of p-toluenesulfonic acid.
37. A reversible iodine transfer does not seem to play a role; see: (a) Newcomb, M.; Sanchez, R. M.; Kaplan, J. J. Am. Chem. Soc. 1987, 109, 1195-1199.
38. (b) Newcomb, M.; Curran, D. P. Acc. Chem. Res. 1988, 21, 206-214.
39. (c) Drury, R. F.; Kaplan, L. J. Am. Chem. Soc. 1972, 94, 3982-3986.