Organocatalytic transfer hydrogenation of cyclic enones

Journal of the American Chemical Society

Volumn 128, Issue 39, 2006, Pages 12662-12663

  Tuttle, Jamison B ^a   Ouellet, Stéphane G ^a   MacMillan, David W C ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DIELS ALDER REACTION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; STEREOSPECIFICITY;

CATALYSIS; CYCLOPARAFFINS; HYDROCARBONS, CYCLIC; HYDROGEN; KETONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 33749516633     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0653066     Document Type: Article

References (23)

1. (a) Akabori, S.; Sakurai, S.; Izumi, Y.; Fujii, Y. Nature 1956, 178, 323.
2. (b) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
3. (c) Knowles, W. S. Angew. Chem., Int. Ed. 2002, 41, 1999.
4. (d) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
5. For recent asymmetric metal-catalyzed reductions, see: (a) Moritani, Y.; Appella, D. H.; Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 6797.
6. (b) Jurkauskas, V.; Sadighi, J. P.; Buchwald, S. L. Org. Lett. 2003, 5, 2417.
7. (c) Lipshutz, B. H.; Servesko, J. M.; Petersen, T. B.; Papa, P. P.; Lover, A. A. Org. Lett. 2004, 6, 1273.
8. Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Roberts, K. I.; Watson, J. D. Molecular Biology of the Cell, 3rd ed.; Garland: New York & London, 2002.
9. (a) Ouellet, S. G.; Tuttle, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 32.
10. (b) Yang, J. W.; Hechavarria Fonseca, M. T.; Vignola, N.; List, B. Angew. Chem., Int Ed. 2005, 44, 108.
11. (c) Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193.
12. Hantzsch, A. Justus Liebigs Ann. Chem. 1882, 215, 1.
13. Furyl imidazolidinone 4 is now commercially available from Aldrich Chemical Co., Milwaukee, WI.
14. Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
15. Three recent examples of iminium activation catalysis from our laboratory include: (a) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.
16. (b) Chen, Y. K.; Yoshida, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 9328.
17. (c) Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051.
18. For a recent review on iminium catalysis see: (d) Lelais, G.; MacMillan, D. W. C. Aldrichimica Acta 2006, 39, 79.
19. For an interesting analysis of the proposed transition state structures for the hydride transfer step with NADH-type compounds, see: (a) Wu, Y.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 2226.
20. (b) Donkersloot, M. C. A.; Buck, H. M. J. Am. Chem. Soc. 1981, 103, 6554.
21. (c) Young, I.; Post, C. B. J. Am. Chem. Soc. 1993, 115, 1964.
22. (d) Wu, Y.; Lai, D. K. W.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 4100.
23. 2O and then purified by silica gel chromatography.