Penultimate group effects in free radical telomerizations of acrylamides

Tetrahedron

Volumn 52, Issue 12, 1996, Pages 4181-4198

  Porter, Ned A ^a   Carter, Randall L ^a   Mero, Christopher L ^a   Roepel, Michael G ^b   Curran, Dennis P ^b  

^a DUKE UNIVERSITY   (United States)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE DERIVATIVE; POLYACRYLAMIDE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0029939023     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00077-4     Document Type: Article

References (21)

1. a.) Porter, N. A.; Giese, B.; and Curran, D. P. Acc. Chem. Res., 1991, 24, 296.
2. b.) Curran, D. P.; Porter, N. A.; Giese, B. "Stereochemistry of Radical Reactions; Concepts, Guidelines, and Synthetic Applications", VCH; Weinheim, 1995.
3. Porter, N. A.; Bruhnke, J. D.; Wu, W. X.; Rosenstein, I. J.; and Breyer, R. A. J. Am. Chem. Soc., 1991, 113, 7788.
4. a.) Curran, D. P.; Shen, W.; Zhang, J.; and Heffner, T. A. J. Am. Chem. Soc., 1990, 112, 6738.
5. b.) Curran, D. P.; Shen, W.; Zhang, J.; Geib, S.J.; Lin, C.-H. Heterocycles, 1994, 37, 1773.
6. Porter, N. A.; Allen, T. A.; and Breyer, R. A. J. Am. Chem. Soc., 1992, 114, 7676.
7. Wu, W. X.; McPhail, A. T.; and Porter, N. A. J. Org. Chem., 1994, 59, 1302.
8. A preliminary report of good erythro selectivity (reference 3a) was later shown to be mistaken (references 3b and 5).
9. Porter, N. A.; Miracle, G. S.; Cannizzaro, S. M.; Carter, R. L.; McPhail, A. T.; and Liu, L. J. Am. Chem. Soc., 1994, 116, 10255.
10. (a) Evans, D. A.; Bilodeau, M. T.; Somers, T. C.; Clardy, J.; Cherry, D.; and Kato, Y. J. Org. Chem., 1991, 56, 5750.
11. (b) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc., 1992, 114, 9434.
12. Significant 1,3 stereocontrol favoring the threo arrangement in free radical additions has recently been achieved through the use of achiral oxazolidinone auxiliaries. Radinov, R.; Mero, C. L.; McPhail, A. T.; Porter, N. A. Tetrahedron Lett, 1995, 36, 8183.
13. Cram, D. J.; and Kopecky, K. R. J. Am. Chem. Soc., 1959, 81, 2748.
14. (a) Fischer, H, Koll, Z. Polym., 1965, 206, 131.
15. (b) Kamachi, M.; Kohno, M.; Liaw, D. J.; and Katsuki, S. Polym. J., 1978, 10, 69.
16. One must also consider the possibility that reaction from other conformers (namely the other amide rotamer) contributes to the observed selectivity in this case.
17. Bergmann, E. D. Chem Rev. 1953, 53, 309.
18. White, E. H.; Lim, H. M. J Org Chem., 1987, 52, 2162.
19. (a) Bodor, N. S.; Kaminski, J. J. US Patent 3,954,985. 4 May 1976.
20. (b) Nazarski, R. B.; Skowronski, R. Pol PL 149,433. (Cl C070263/04) 28 Feb 1990.
21. Gage, J. R.; Evans, D. A. Org. Synth. 1989, 68, 83.