Asymmetric Hydrocyanation of Hydrazones Catalyzed by Lanthanide - PYBOX Complexes

Organic Letters

Volumn 6, Issue 2, 2004, Pages 153-155

  Keith, John M ^a,b   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

^b JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CHLORIDE; CYANIC ACID; ERBIUM; HYDRAZONE DERIVATIVE; LANTHANIDE;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; HYDROCYANATION;

CATALYSIS; HYDRAZONES; HYDROGEN CYANIDE; LANTHANOID SERIES ELEMENTS; MOLECULAR STRUCTURE;

EID: 0842263621     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035844c     Document Type: Article

References (25)

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2. For reviews, see: (a) Mori, A.; Inoue, S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York; 1999, Chapter 28. (b) Vachal, P.; Jacobsen, E. N. In Comprehensive Asymmetric Catalysis Supplement 1; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York; 2003, Chapter 28.
3. For recent examples of enantioselective additions to hydrazones, see: (a) Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura M. J. Am. Chem. Soc. 2003, 125, 6610-6611. (b) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640-5641. (c) Kobayashi, S.; Shimizu, H.; Yamashita, Y.; Ishitani, H.; Kobayashi, J. J. Am. Chem. Soc. 2002, 124, 13678-13679.
4. For recent examples of enantioselective additions to hydrazones, see: (a) Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura M. J. Am. Chem. Soc. 2003, 125, 6610-6611. (b) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640-5641. (c) Kobayashi, S.; Shimizu, H.; Yamashita, Y.; Ishitani, H.; Kobayashi, J. J. Am. Chem. Soc. 2002, 124, 13678-13679.
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19. Lanthanum triflates and alkoxides were found to be ineffective catalysts, inducing only low substrate conversion.
20. Only N-benzoyl, N-2-furanoyl, and N-2-thiophenoyl hydrazones displayed any reactivity under these reaction conditions, with both N-2-furanoyl and N-2-thiophenoyl derivatives undergoing hydrocyanation to very low conversion. Other hydrazones examined included N-tosyl, N-nosyl, N-formyl, N-acetyl, N-octoyl, N-phenylacetyl, N-phenyl, N-2,4-dinitrophenyl, and N-Boc derivatives.
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23. Aged chloroform, which can contain chlorine and HCl, induced hydrazone oxidation to afford several products, one of which was identified as 2,5-diphenyl-1,3,4-oxadiazole. Interestingly, treatment of a hydrazone with DDQ gives an identical product ratio as aged chloroform.
24. Combination of MeOH and TMSCN afforded better conversions and ees than TMSCN alone or preformed HCN.
25. 3 ratios of 1.2-2.0 may be employed with no effect on ee or yield, although catalysts prepared with 2 equiv of ligand display better solubility.