Catalytic asymmetric Strecker synthesis. Preparation of enantiomerically pure α-amino acid derivatives from aldimines and tributyltin cyanide or achiral aldehydes, amines, and hydrogen cyanide using a chiral zirconium catalyst

Journal of the American Chemical Society

Volumn 122, Issue 5, 2000, Pages 762-766

  Ishitani, Haruro ^a,b   Komiyama, Susumu ^a,b   Hasegawa, Yoshiki ^a,b   Kobayashi, Shu ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; AMINO ACID DERIVATIVE; CYANIDE; HYDROGEN CYANIDE; TRIBUTYLTIN;

AMINO ACID SYNTHESIS; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034624418     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9935207     Document Type: Article

References (42)

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7. Recently, catalytic asymmetric cyanation reactions of Schiff bases have been reported. (a) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910. (b) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. (c) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315. (d) Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 3186. (e) Krueger, C. A.; Kuntz, K. W.; Dzieba, C. D.; Wirschum, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284. (f) Corey, E. J.; Grogan, M. J. Org. Lett 1999, 1, 157. In all these cases, no example of the three-component reactions that succeed to the original Strecker reaction was reported. In addition, lower selectivities were obtained using Shiff bases derived from aliphatic aldehydes, which restricts use of these reactions for α-amino acid syntheses.
8. Recently, catalytic asymmetric cyanation reactions of Schiff bases have been reported. (a) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910. (b) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. (c) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315. (d) Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 3186. (e) Krueger, C. A.; Kuntz, K. W.; Dzieba, C. D.; Wirschum, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284. (f) Corey, E. J.; Grogan, M. J. Org. Lett 1999, 1, 157. In all these cases, no example of the three-component reactions that succeed to the original Strecker reaction was reported. In addition, lower selectivities were obtained using Shiff bases derived from aliphatic aldehydes, which restricts use of these reactions for α-amino acid syntheses.
9. Recently, catalytic asymmetric cyanation reactions of Schiff bases have been reported. (a) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910. (b) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. (c) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315. (d) Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 3186. (e) Krueger, C. A.; Kuntz, K. W.; Dzieba, C. D.; Wirschum, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284. (f) Corey, E. J.; Grogan, M. J. Org. Lett 1999, 1, 157. In all these cases, no example of the three-component reactions that succeed to the original Strecker reaction was reported. In addition, lower selectivities were obtained using Shiff bases derived from aliphatic aldehydes, which restricts use of these reactions for α-amino acid syntheses.
10. Recently, catalytic asymmetric cyanation reactions of Schiff bases have been reported. (a) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910. (b) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. (c) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315. (d) Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 3186. (e) Krueger, C. A.; Kuntz, K. W.; Dzieba, C. D.; Wirschum, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284. (f) Corey, E. J.; Grogan, M. J. Org. Lett 1999, 1, 157. In all these cases, no example of the three-component reactions that succeed to the original Strecker reaction was reported. In addition, lower selectivities were obtained using Shiff bases derived from aliphatic aldehydes, which restricts use of these reactions for α-amino acid syntheses.
11. Recently, catalytic asymmetric cyanation reactions of Schiff bases have been reported. (a) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910. (b) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. (c) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315. (d) Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 3186. (e) Krueger, C. A.; Kuntz, K. W.; Dzieba, C. D.; Wirschum, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284. (f) Corey, E. J.; Grogan, M. J. Org. Lett 1999, 1, 157. In all these cases, no example of the three-component reactions that succeed to the original Strecker reaction was reported. In addition, lower selectivities were obtained using Shiff bases derived from aliphatic aldehydes, which restricts use of these reactions for α-amino acid syntheses.
12. Recently, catalytic asymmetric cyanation reactions of Schiff bases have been reported. (a) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910. (b) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. (c) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315. (d) Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 3186. (e) Krueger, C. A.; Kuntz, K. W.; Dzieba, C. D.; Wirschum, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284. (f) Corey, E. J.; Grogan, M. J. Org. Lett 1999, 1, 157. In all these cases, no example of the three-component reactions that succeed to the original Strecker reaction was reported. In addition, lower selectivities were obtained using Shiff bases derived from aliphatic aldehydes, which restricts use of these reactions for α-amino acid syntheses.
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