Enantioselective organocatalytic hydride reduction

Journal of the American Chemical Society

Volumn 127, Issue 1, 2005, Pages 32-33

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

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; DIHYDROPYRIDINE; HYDROGEN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE; REDUCTION;

ALDEHYDES; DIHYDROPYRIDINES; HYDROGEN; IMIDAZOLIDINES; IMINES; MODELS, MOLECULAR; OXIDATION-REDUCTION; PROLINE; STEREOISOMERISM;

EID: 11844277087     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja043834g     Document Type: Article

References (15)

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) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
4. Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Roberts, K.; Watson, J. D. Molecular Biology of the Cell, 3rd ed.; Garland: New York & London, 2002.
5. This complete study was first presented orally at the Lilly Grantee Symposium, Indianapolis, IN, March 1, 2003.
6. The conjugate reduction of Wieland-Miescher ketone has previously been accomplished with Hantzsch ester: (a) Pandit, U. K.; Mas Cabré, F. R.; Gase, R. A.; de Nie-Sarink, M. J. J. Chem. Soc., Chem. Commun. 1974, 627. (b) de Nie-Sarink, M. J.; Pandit, U. K. Tetrahedron Lett. 1979, 26, 2449
7. The conjugate reduction of Wieland-Miescher ketone has previously been accomplished with Hantzsch ester: (a) Pandit, U. K.; Mas Cabré, F. R.; Gase, R. A.; de Nie-Sarink, M. J. J. Chem. Soc., Chem. Commun. 1974, 627. (b) de Nie-Sarink, M. J.; Pandit, U. K. Tetrahedron Lett. 1979, 26, 2449
8. (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
9. (b) Austin, J. F.; MacMillan, D. W. C. J Am. Chem. Soc. 2002, 124, 1172.
10. Keinan, E.; Greenspoon, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford. 1991; Vol. 8, Chapter 3.5, p 523.
11. (a) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223.
12. (b) Lavilla, R. J. Chem. Soc., Perkin Trans. 1 2002, 1141.
13. Hantzsch, A. Justus Liebigs Ann. Chem. 1882, 215, 1.
14. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
15. (b) Lipshutz, B. H.; Servesko, J. M. Angew. Chem., Int. Ed. 2003, 41, 4789.