Catalytic diastereoselective reductive Claisen rearrangement

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2743-2745

  Miller, Steven P ^a   Morken, James P ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

BENZENE DERIVATIVES; CATALYSIS; STEREOISOMERISM;

EID: 0037043495     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026273b     Document Type: Article

References (33)

1. For excellent reviews, see: (a) Chai, Y.; Hong, S.; Linday, H. A.; McFarland, C.; McIntosh, M. C. Tetrahedron 2002, 58, 2905.
2. (b) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 827.
3. (c) Blechert, S. Synthesis 1989, 71.
4. (d) Ziegler, F. E. Acc. Chem. Res. 1977, 589. For examples of enantioselective ester enolate Claisen rearrangements, see:
5. (e) Corey, E. J.; Lee, D. H. J. Am. Chem. Soc. 1991, 113, 4026.
6. (f) Kazmaier, U.; Krebs, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2012.
7. (g) Kazmaier, U.; Mues, H.; Krebs, A. Chem. Eur. J. 2002, 8, 1850. For an example of an enantioselective acyl-Claisen rearrangement, see:
8. (h) Yoon, T. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 2911. For an example of a catalytic enantioselective Claisen rearrangement, see:
9. Abraham, L.; Czerwonka, R.; Hiersemann, M. Angew. Chem., Int. Ed. 2001, 40, 4700.
10. (a) Mascarenhas, C. M.; Duffey, M. O.; Liu, S. Y.; Morken, J. P. Org. Lett. 1999, 1, 1427.
11. (b) Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202.
12. (c) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528.
13. (d) Mascarenhas, C. M.; Miller, S. P.; White, P. S.; Morken, J. P. Angew. Chem., Int. Ed. 2001, 40, 601.
14. (e) Zhao, C. X.; Taylor, S. J.; Bass, J.; Morken, J. P. Org. Lett. 2001, 3, 2839.
15. (f) Zhao, C. X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
16. Me-DuPhos: 1,2-bis(dimethylphospholano)benzene. See: Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653.
17. (a) Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897.
18. (b) Ireland, R. E.; Willard, A. K. Tetrahedron Lett. 1975, 46, 3975.
19. (c) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
20. (d) Ireland, R. E.; Varney, M. D. J. Am. Chem. Soc. 1984, 106, 3668.
21. (e) Ireland, R. E.; Wipf, P.; Armstrong, J. D. J. Org. Chem. 1991, 56, 650.
22. (f) Ireland, R. E.; Wipf, P.; Xiang, J. N. J. Org. Chem. 1991, 56, 3572.
23. For one example of a reductive Claisen rearrangement, see: Cambie, R. C.; Milbank, J. B. J.; Rutledge, P. S. Org. Prep. Proced. Int. 1997, 29, 367.
24. While we have not been able to observe the presumed intermediate silylketene acetal in any of our experiments, the reactions products are racemic.
25. For a similar Ireland-Claisen rearrangement with a cyclic allylic ester that proceeds in low stereoselection, see: Bartlett, P. A.; Pizzo, C. F. J. Org. Chem. 1981, 46, 3896.
26. Muraoka, T.; Matsuda, I.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 9552.
27. For elegant examples of chemoselective Ireland-Claisen rearrangements involving selective deprotonation, see: (a) Burke, S. D.; Fobare, W. F.; Pacofsky, G. J. J. Org. Chem. 1983, 48, 5221.
28. (b) Paterson, I.; Hulme, A. N. J. Org. Chem. 1995, 60, 3288.
29. (c) Pratt, L. M.; Beckett, R. P.; Bellamy, C. L.; Corkill, D. J.; Cossins, J.; Courtney, P. F.; Davies, S. J.; Davidson, A. H.; Drummond, A. H.; Helfrich, K.; Lewis, C. N.; Mangan, M.; Martin, F. M.; Miller, K.; Nayee, P.; Ricketts, M. L.; Thomas, W.; Todd, R. S.; Whittaker, M. Bioorg. Med. Chem. Lett. 1998, 8, 1359.
30. For reports of presumed catalytic reductive enolate generation followed by C-C bond formation, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809.
31. (b) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005.
32. (c) Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331.
33. (d) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237.