Reduction of carbon-carbon double bonds using organocatalytically generated diimide

Journal of Organic Chemistry

Volumn 73, Issue 23, 2008, Pages 9482-9485

  Smit, Christian ^a   Fraaije, Marco W ^b   Minnaard, Adriaan J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; HYDRATES; HYDROGENATION;

CARBON DOUBLE BONDS; CHEMICAL EQUATIONS; EFFICIENT METHODS; HYDRAZINE HYDRATES; IN-SITU; ONE STEPS; VITAMIN B;

CHEMICAL BONDS;

ALLYL COMPOUND; BENZYL DERIVATIVE; CYCLOPROPANE; FLAVINE ADENINE NUCLEOTIDE; HYDRAZINE; IMIDE; ISOMERASE; RIBOFLAVIN; TRANSITION ELEMENT; ALDEHYDE; CARBON; HYDRAZINE DERIVATIVE; HYDROGEN; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL BOND; EPIMERIZATION; HYDROGENATION; HYDROGENOLYSIS; ISOMERIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION KINETICS; PROTEIN SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; REDUCTION; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ORGANIC CHEMISTRY; PROCEDURES;

ALDEHYDES; CARBON; CATALYSIS; CHEMISTRY, ORGANIC; HYDRAZINES; HYDROGEN; IMIDES; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; RIBOFLAVIN; SOLVENTS;

EID: 57449101056     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801588d     Document Type: Article

References (26)

1. Corey E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley: New York, 1989.
2. Handbook of Homogeneous Hydrogenation; de Vries J. G., Elsevier, C. J., Eds.; Wiley-VCH: New York, 2007.
3. Wilkinson, H. S.; Hett, R.; Tanoury, G. J.; Senanayake, C. H.; Wald, S. A. Org. Proc. Res. Dev. 2000, 4, 567-570.
4. Galletti, A. M. R.; Bonaccorsi, F.; Calvani, F.; Di Bugno, C. Catal. Commun. 2006, 7, 896-900.
5. (a) Smith, G. V.; Roth, J. A.; Desai, D. S.; Kosco, J. L. J. Catal. 1973, 30, 79-85.
6. (b) Smith, G. V.; Wang, Y.; Song, R.; Jackson, M. Mol. Catal. Today 1998, 44, 119-127.
7. (a) Nakai, T.; Yajima, A.; Akasaka, K.; Kaihoku, T.; Ohtaki, M.; Nukada, T.; Ohrui, H.; Yabuta, G. Biosci. Biotechnol. Biochem. 2005, 69, 2401-2408.
8. (b) Schwartz, B. D.; Hayes, P. Y.; Kitching, W.; De Voss, J. J. J. Org. Chem. 2005, 70, 3054-3065.
9. (c) Rakoff, H.; Rohwedder, W. K. Lipids 1992, 27, 567-569.
10. Mori, K.; Ohtaki, T.; Ohrui, H.; Berkebile, D. R.; Carlson, D. A. Eur. J. Org. Chem. 2004, 1089-1096.
11. Dandapani, S.; Jeske, M.; Curran, D. P. J. Org. Chem. 2005, 70, 9447-9462.
12. Yajima, A.; Qin, Y.; Zhou, X.; Kawanishi, N.; Xiao, X.; Wang, J.; Zhang, D.; Wu, Y.; Nukada, T.; Yabuta, G.; Qi, J.; Asano, T.; Sakagami, Y. Nature Chem. Biol. 2008, 4, 235-237.
13. Nishimura, T.; Guo, X.-X.; Uchiyama, N.; Katoh, T.; Hayashi, T. J. Am. Chem. Soc. 2008, 130, 1576-1577.
14. Pasto, D. J.; Taylor, R. T. Reductions with Diimide in Organic Reactions; V Paquette L. A., Ed.; J. Wiley & Sons: New York, 1991; Vol. 40, pp 91-150.
15. o-Nitrophenylsulfonylhydrazide (2-nitrobenzenesulfonhydrazide, NBSH) has been introduced as an easy to handle diimide precursor, see: Haukaas, M. H.; O'Doherty, G. A. Org. Lett. 2002, 4, 1771-1774.
16. Anhydrous hydrazine is not easily prepared, however, and in general not commercially available.
17. Imada, Y.; Iida, H.; Naota, T. J. Am. Chem. Soc. 2005, 127, 14544-14545.
18. In the case of flavin as a cofactor, the enzyme normally facilitates this step.
19. Kemal, C.; Chan, T. W.; Bruice, T. C. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 405-409.
20. Gelalcha, F. G. Chem. Rev. 2007, 107, 3338-3361.
21. Imada, Y.; Iida, H.; Murahashi, S.-I.; Naota, T. Angew. Chem., Int. Ed. 2005, 44, 1704-1706.
22. 5 ethyl group appears in the same region as the signal from the ribose chain. Peak broadening as a result of radical species present, however, blurs these NMR data. See: Bruice, T. C.; Yano, Y. J. Am. Chem. Soc. 1975, 97, 5263-5271.
23. Minidis, A. B. E.; Bäckvall, J.-E. Chem. Eur. J. 2001, 7, 297-302.
24. Lacombe, P.; Castagner, B.; Gareau, Y.; Ruel, R. Tetrahedron Lett. 1998, 39, 6785-6786.
25. Buszek, K. R.; Brown, N. J. Org. Chem. 2007, 72, 3125-3128.
26. Wideman, L. G. The Goodyear Tire & Rubber Company, US Patent 4452 950, 1985.