Intramolecular addition of acyl radicals to a-substituted vinylogous carbonates: Demonstrating the effect of ring size on acyclic stereocontrol

Chemical Communications

Volumn 1, Issue 23, 2001, Pages 2504-2505

  Evans, P Andrew ^a   Raina, Sushil ^b   Ahsan, Khalid ^a  

^a INDIANA UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONIC ACID DERIVATIVE; RADICAL;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; REDUCTION; STEREOCHEMISTRY;

EID: 0035824368     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b106766b     Document Type: Article

References (27)

1. C. J. Moody and M. Davies, in Studies in Natural Product Chemistry, ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1992, vol. 10, pp. 201-239;
2. J.-C. Harmange and B. Figadere, Tetrahedron: Asymmetry, 1993, 4, 1711;
3. E. Alvarez, M.-L. Candenas, R. Perez, J. L. Ravelo and J. D. Martin, Chem. Rev., 1995, 95, 1953;
4. J. O. Hoberg, Tetrahedron, 1998, 54, 12631
5. I. Ryu, N. Sonoda and D. P. Curran, Chem. Rev., 1996, 96, 177;
6. C. Chatgilialoglu, D. Crich, M. Komatsu and I. Ryu, Chem. Rev., 1999, 99, 1991.
7. P. A. Evans and J. D. Roseman, Tetrahedron Lett., 1995, 36, 31;
8. P. A. Evans and J. D. Roseman, J. Org. Chem., 1996, 61, 2252;
9. P. A. Evans, J. D. Roseman and L. T. Garber, J. Org. Chem., 1996, 61, 4880.
10. P. A. Evans, V. S. Murthy, J. D. Roseman and A. L. Rheingold, Angew. Chem., Int. Ed., 1999, 38, 3175.
11. E. Lee, S.-K. Yoo, H. Choo and H. Y. Song, Tetrahedron Lett., 1998, 39, 317
12. Yuasa, W. Sato and S. Shibuya, Synth. Commun., 1997, 27, 573;
13. G. Pandey, S. Hajra, M. K. Ghorai and R. Kumar, J. Org. Chem., 1997, 62, 5966;
14. N. Hori, H. Matsukura, G. Matsuo and T. Nakata, Tetrahedron Lett., 1999, 40, 2811;
15. M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
16. P. A. Evans and J. D. Roseman, Tetrahedron Lett., 1997, 38, 5249;
17. P. A. Evans and T. Manangan, Tetrahedron Lett., 1997, 38, 8165;
18. P. A. Evans and T. Manangan, J. Org. Chem., 2000, 65, 4523.
19. Y. Guindon, J.-F. Lavallee, L. Boisvert, C. Chabot, D. Delorme, C. Yoakim, D. Hall, R. Lemieux and B. Simoneau, Tetrahedron Lett., 1991, 32, 27;
20. K. Durkin, D. Liotta, J. Rancourt, J.-F. Lavallee, L. Boisvert and Y. Guindon, J. Am. Chem. Soc., 1992, 114, 4912.
21. E. Lee and S. J. Choi, Org. Lett., 1999, 1, 1127.
22. D. P. Curran, N. D. Porter and B. Giese, in Stereochemistry of Radical Reactions: Concepts, Guidelines and Synthetic Applications, VCH Publishers, New York, 1995, pp. 147-177.
23. C. Chatgilialoglu, Acc. Chem. Res., 1992, 25, 188;
24. C. Chatgilialoglu, C. Ferreri and T. Gimisis, in The Chemistry of Organic Silicon Compounds, ed. S. Rappoport and Y. Apeloig, Wiley, London, 1998, vol. 2, chapter 25, pp. 1539.
25. K. C. Nicolaou, C. A. Veale, C.-K. Hwang, J. Hutchinson, C. V. C. Prasad and W. W. Ogilvie, Angew. Chem., Int. Ed. Engl., 1991, 30, 299.
26. P. A. Evans, J. D. Roseman and L. T. Garber, Synth. Commun., 1996, 26, 4685.
27. D. Batty and D. Crich, Synthesis, 1990, 273.