Hydrogen bond mediated enantioselectivity of radical reactions

Angewandte Chemie - International Edition

Volumn 43, Issue 43, 2004, Pages 5849-5851

  Aechtner, Tobias ^a   Dressel, Martina ^a   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Asymmetric synthesis; Cyclization; Enantioselectivity; Hydrogen bonds; Radical reactions

Indexed keywords

HYDROGEN BONDS; INITIATORS (CHEMICAL); MOLECULAR DYNAMICS; REACTION KINETICS; TIN COMPOUNDS;

CYCLIZATION; ENANTIOSELECTIVITIES; RADICAL REACTIONS;

FREE RADICALS;

RADICAL;

ARTICLE; ASYMMETRIC SYNTHESIS; CYCLIZATION; ENANTIOSELECTIVITY; HYDROGEN BOND; RADICAL REACTION; REACTION ANALYSIS;

EID: 8844275954     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461222     Document Type: Article

References (39)

1. General reviews: a) Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001;
2. b) T. Linker, M. Schmittel, Radikale und Radikalionen in der Organischen Synthese, Wiley-VCH, Weinheim, 1998;
3. c) D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996.
4. Reviews on enantioselective radical reactions: a) M. P. Sibi, S. Manyer, J. Zimmerman, Chem. Rev. 2003, 103, 3263-3295;
5. b) G. Bar, A. Parsons, Chem. Soc. Rev. 2003, 32, 251-263;
6. c) M. Sibi, N. A. Porter, Ace. Chem. Res. 1999, 32, 163-171;
7. d) P. Renaud, M. Gerster, Angew. Chem. 1998, 770, 2704-2722; Angew. Chem. Int. Ed. 1998, 37, 2562-2579.
8. d) P. Renaud, M. Gerster, Angew. Chem. 1998, 770, 2704-2722; Angew. Chem. Int. Ed. 1998, 37, 2562-2579.
9. a) D. Nanni, D. P. Curran, Tetrahedron: Asymmetry 1996, 7, 2417-2422;
10. b) M. Blumenstein, K. Schwarzkipf, J. O. Metzger, Angew. Chem. 1997, 109, 245-247; Angew. Chem. Int. Ed. Engl. 1997, 36, 235-236;
11. b) M. Blumenstein, K. Schwarzkipf, J. O. Metzger, Angew. Chem. 1997, 109, 245-247; Angew. Chem. Int. Ed. Engl. 1997, 36, 235-236;
12. c) D. Dakternieks, K. Dunn, V. T. Perchyonok, C. H. Schiesser, Chem. Commun. 1999, 1665-1666;
13. d) D. Dakternieks, V.T. Perchyonok, C. H. Schiesser, Tetrahedron: Asymmetry 2003, 14, 3057-3068;
14. e) M. Blumenstein, M. Lemmler, A. Hayen, J. O. Metzger, Tetrahedron: Asymmetry 2003, 14, 3069-3077, and references therein.
15. First original reports: a) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481-482;
16. b) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, J. Org. Chem. 1995, 60, 3576-3577;
17. c) J. H. Wu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030;
18. d) M. Nishida, H. Hayashi, A. Nishida, N. Kawahara, Chem. Commun. 1996, 579-580;
19. e) M. P. Sibi, J. Ji, J. H. Wu, S. Gürtler, N. A. Porter, J. Am. Chem. Soc. 1996, 118, 9200-9201;
20. f) A.-R. Fhal, P. Renaud, Tetrahedron Lett. 1997, 38, 2661-2664.
21. a) J. L. Garcia Ruano, M. M. Cifuentes, A. Lorente, J. H. Rodriguez Ramos, Tetrahedron: Asymmetry 1999, 10, 4607-4618;
22. b) A. P. Kozikowski, P. W. Shum, A. Basu, J. S. Lazo, J. Med. Chem. 1991, 34, 2420-2430.
23. a) A. L. J. Beckwith, Tetrahedron 1981, 37, 3073-3100;
24. b) A. L. J. Beckwith, CH. Schiesser, Tetrahedron 1985, 41, 3925-3941;
25. c) B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K.J. Kulicke, F. Trach, Org. React. 1996, 48, 301-856.
26. T. Bach, H. Bergmann, B. Grosch, K. Harms, E. Herdtweck, Synthesis 2001, 1395-1405.
27. For the use of similar amides as chiral auxiliaries in radical reactions, see J. G. Stack, D. P. Curran, S. V. Geib, J. Rebek, Jr., P. Ballester, J. Am. Chem. Soc. 1992, 114, 7007-7018.
28. Examples: a) T. Bach, H. Bergmann, K. Harms, Angew. Chem. 2000, 112, 2391-2393; Angew. Chem. Int. Ed. 2000, 39, 2302-2304;
29. Examples: a) T. Bach, H. Bergmann, K. Harms, Angew. Chem. 2000, 112, 2391-2393; Angew. Chem. Int. Ed. 2000, 39, 2302-2304;
30. b) T. Bach, H. Bergmann, B. Grosch, K. Harms, J. Am. Chem. Soc. 2002, 124, 7982-7990;
31. c) T. Bach, T. Aechtner, B. Neumüller, Chem. Eur. J. 2002, 8, 2464-2475;
32. d) T. Bach, B. Grosch, T. Strassner, E. Herdtweck, J. Org. Chem. 2003, 68, 1107-1116;
33. e) B. Grosch, C. N. Orlebar, E. Herdtweck, M. Kaneda, T. Wada, Y. Inoue, T. Bach, Chem. Eur. J. 2004, 10, 2179-2189.
34. 17NO (167.248) (%): calcd. C 71.81, H 10.25; found C 71.91, H 10.25.
35. H. Bergmann, B. Grosch, S. Sitterberg, T. Bach, J. Org, Chem. 2004, 69, 970-973.
36. a) D. Enders, R. Groebner, G. Raabe, J. Runsink, Synthesis 1996, 941-948;
37. b) M. Brenner, D. Seebach, Helv. Chim. Acta 1999, 82, 2365-2379;
38. c) Y.-G. Suh, S.-A. Kim, J.-K. Jung, D.-Y. Shin, K.-H. Min, B.-A. Koo, H.-S. Kim,Angew. Chem. 1999, 111, 3753-3755; Angew. Chem. Int. Ed. 1999, 38, 3545-3547.
39. c) Y.-G. Suh, S.-A. Kim, J.-K. Jung, D.-Y. Shin, K.-H. Min, B.-A. Koo, H.-S. Kim,Angew. Chem. 1999, 111, 3753-3755; Angew. Chem. Int. Ed. 1999, 38, 3545-3547.