Diastereoselective conjugate radical additions to β-pyranones

Synlett

Volumn , Issue 20, 2007, Pages 3193-3197

  Sibi, Mukund P ^a   Yu, Arvin ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

pyranones; Conjugate addition; Diastereoselectivity; Radical reaction; Tandem reactions

Indexed keywords

BETA PYRANONE DERIVATIVE; PYRONE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; NUCLEAR MAGNETIC RESONANCE; RADICAL REACTION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 37749036044     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992381     Document Type: Article

References (44)

1. (a) Radicals in Organic Synthesis, Vol. 1 and 2; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001.
2. (b) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2003, 103, 3263.
3. (c) Zimmerman, J.; Sibi, M. P. Top. Curr. Chem. 2006, 263, 107.
4. For a recent review on tandem radical reactions, see: Albert, M.; Fensterbank, L.; Lacote, E.; Malacria, M. Top. Curr. Chem. 2006, 264, 1.
5. Sibi, M. P.; Zimmerman, J. J. Am. Chem. Soc. 2006, 128, 13346.
6. van der Deen, H.; Kellogg, R. M.; Feringa, B. L. Org. Lett. 2000, 2, 1593.
7. For work from Fraser-Reid and co-workers, see: (a) Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1992, 57, 1065.
8. (b) Fraser-Reid, B.; Holder, N. L.; Hicks, D. R.; Walker, D. L. Can. J. Chem. 1977, 55, 3978.
9. (c) Benko, Z.; Fraser-Reid, B.; Mariano, P. S.; Beckwith, A. L. J. J. Org. Chem. 1988, 53, 2066.
10. For selected examples on the use of β-pyranones in synthesis from other groups, see: (d) Babu, R. S.; Zhou, M.; O'Doherty, G. A. J. Am. Chem. Soc. 2004, 121, 3428.
11. (e) Guo, H.; O'Doherty, G. A. Org. Lett. 2005, 7, 3921.
12. (f) Shan, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 5149.
13. (g) Comely, A. C.; Eelkema, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 8714.
14. (h) van den Heuvel, M.; Cuiper, A. D.; van der Deen, H.; Kellogg, R. M.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 1655.
15. (i) Fürstner, A.; Feyen, F.; Prinz, H.; Waldmann, H. Angew. Chem. Int. Ed. 2003, 42, 5361.
16. (j) Krishnan, K. S.; Smitha, M.; Suresh, E.; Radhakrishnan, K. V. Tetrahedron 2006, 62, 12345.
17. (k) Panfil, I.; Chmielewski, M. Tetrahedron 1985, 41, 4713.
18. (l) Giese, B.; Witzel, T. Tetrahedron Lett. 1987, 28, 2571.
19. Compound 5 was prepared in racemic form using a literature procedure. See: Caddick, S.; Khan, S.; Frost, L. M.; Cheung, S.; Pairaudeau, G. Tetrahedron 2000, 56, 8953.
20. All new compounds showed analytical and spectral characteristics consistent with their structure. An experimental procedure and spectral data for select products are provided.
21. For recent reviews ,see: (a) Baguley, P. A.; Walton, J. C. Angew. Chem. Int. Ed. 1998, 37, 3072.
22. (b) Parsons, A. F. Chem. Br. 2002, 38, 42.
23. Alternatives to tin hydrides - selected examples: (c) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
24. (d) Leca, D.; Fensterbank, L.; Lacote, E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858.
25. (e) Studer, A.; Amrein, S. Synthesis 2002, 835.
26. (f) Graham, S. R.; Murphy, J. A.; Kennedy, A. R. J. Chem. Soc., Perkin Trans. 1 1999, 3071.
27. (g) Studer, A.; Amrein, S.; Schleth, F.; Schulte, T.; Walton, J. C. J. Am. Chem. Soc. 2003, 125, 5726.
28. (h) Cho, D. H.; Jang, D. O. Bull. Korean Chem. Soc. 2003, 24, 15.
29. (i) Khan, T. A.; Tripoli, R.; Crawford, J. J.; Martin, C. G.; Murphy, J. A. Org. Lett. 2003, 5, 2971.
30. For an example on the use of functionalized radicals in conjugate addition, see: Sibi, M. P.; Guerrero, M. Synthesis 2005, 1528.
31. For related examples of stereochemical control with 6-acyloxy-3- pyranones, see: (a) Bashiardes, G.; Cano, C.; Mauze, B. Synlett 2005, 587.
32. (b) Sugawara, K.; Imanishi, Y.; Hashiyama, T. Heterocycles 2007, 71, 597.
33. For selected review articles, see: (a) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163.
34. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
35. (c) Curran, D. P. Aldrichimica Acta 2000, 33, 104.
36. (d) Rosenstein, I. J. In Radicals in Organic Synthesis, Vol. 1; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: New York, 2001, 50-71.
37. For intermolecular radical addition and allyl stannane trapping, see: (e) Sibi, M. P.; Chen, J. J. Am. Chem. Soc. 2001, 123, 9472.
38. (f) Sibi, M. P.; Aasmul, M.; Hasegawa, H.; Subramanian, T. Org. Lett. 2003, 5, 2883.
39. (g) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090.
40. (h) Ueda, M.; Miyabe, H.; Sugino, H.; Miyata, O.; Naito, T. Angew. Chem. Int. Ed. 2005, 44, 6190.
41. Compounds 8 and 11 were prepared following literature procedures. Commercially available enantiopure (R)- and (S)-2-furyl ethanols were converted into 8 and 11, respectively. See: (a) Ref. 5a.
42. (b) Zhou, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 4339.
43. (c) Zhou, M.; O'Doherty, G. A. J. Org. Chem. 2007, 72, 2485.
44. (d) Yonghong, G.; Fangning, Z.; Xinfu, P. J. Chem. Res., Synop. 1999, 488.