Memory of chirality in the transannular cyclization of cyclodecenyl radicals

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2713-2716

  Dalgard, Jackline E ^a   Rychnovsky, Scott D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODECANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATIONAL TRANSITION; CYCLIZATION; ENANTIOSELECTIVITY; MOLECULAR STABILITY; REACTION ANALYSIS;

ALKANES; ALKENES; BICYCLO COMPOUNDS; CYCLIZATION; FREE RADICALS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 4344617825     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049038x     Document Type: Article

References (19)

1. (a) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163-171.
2. (b) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: New York, 1996.
3. Kawabata, T.; Fuji, K. Top. Stereochem. 2003, 23, 175-205.
4. In alkylations: (a) Carlier, P. R.; Zhao, H.; DeGuzman, J.; Lam, P. C.-H. J. Am. Chem. Soc. 2003, 125, 11482-11483. (b) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748.
5. In alkylations: (a) Carlier, P. R.; Zhao, H.; DeGuzman, J.; Lam, P. C.-H. J. Am. Chem. Soc. 2003, 125, 11482-11483. (b) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748.
6. (a) Curran, D. P.; Liu, W.; Chen, C. H.-T. J. Am. Chem. Soc. 1999, 121, 11012-11013.
7. (b) Giese, B.; Wettstein, P.; Stahelin, C.; Barbosa, F.; Neuburger, M.; Zehnder, M.; Wessig, P. Angew. Chem., Int. Ed. 1999, 38, 2586-2587.
8. (c) Sauer, S.; Schumacher, A.; Barbosa, F.; Giese, B. Tetrahedron Lett. 1998, 39, 3685-3688.
9. (a) Buckmelter, A. J.; Kim, A. I.; Rychnovsky, S. D. J. Am. Chem. Soc. 2000, 122, 9386-9390.
10. (b) Buckmelter, A. J.; Powers, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 1998, 120, 5589-5590.
11. Beckwith, A. L. J.; Bowry, V. W.; Schiesser, C. H. Tetrahedron 1991, 47, 121-130.
12. (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
13. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
14. (c) Grubbs, R. H.; Kirkland, T. A. J. Org. Chem. 1997, 62, 7310-7318.
15. (a) Lee, C. W.; Grubbs, R. H. Org. Lett. 2000, 2, 2145-2147.
16. (b) Furstner, A.; Muller, T. Synlett 1997, 1010-1011.
17. (b) Furstner, A.; Langemann, K. Synthesis 1997, 792-803.
18. Selective dihydroxylation with α-AD-mix (60% conversion) returned the starting cyclodecene of the same isomeric ratio.
19. 1H NMR at -30°C and varied slightly at different temperatures: 1:1.71 (-30°C), 1:1.66 (-20°C), 1:1.60 (-10°C).