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Synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids from β-chloroaldimines

(1991) TETRAHEDRON. 47(26). p.4723-4738
Author
Organization
Abstract
A variety of hydrogen cyanide adducts of beta-chloroaldimines using acetone cyanohydrin were prepared. The reactive behaviour of these alpha-amino-gamma-chloronitriles towards bases was investigated with the aim to generate 1-aminocyclopropanecarbonitriles, which are precursors for the potentially plant growth regulating 1-aminocyclopropanecarboxylic acids. The synthesis of 1-amino-2,2-dimethylcyclopropanecarboxylic acid (= 2,3-methanovaline) by a reaction sequence involving addition of hydrogen cyanide across beta-chloroaldimines, ring closure to functionalized cyclopropanes and acidic hydrolysis was accomplished. Alternatively the hydrogen cyanide adducts of beta-chloroaldimines were converted into alpha-(N-benzylidene)amino-gamma-chloronitriles, which were ring closed with base and hydrolyzed to afford 1-amino-2,2-dialkylcyclopropanecarbonitriles, the latter serving again as substrates for the hydrolytic conversion into the corresponding 1-amino-2,2-dialkylcyclopropanecarboxylic acids (exemplified for 1-amino-2,2-dimethylcyclopropanecarboxylic acid).
Keywords
ALGA GRATELOUPIA-CARNOSA, CYCLOPROPANE AMINO-ACIDS, 2, 2-DIALKYL-1-AMINOCYCLOPROPANECARBOXYLIC ACIDS, ETHYLENE BIOSYNTHESIS, CHLOROIMINES, KETIMINES, CHEMISTRY, IMINES

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Chicago
De Kimpe, Norbert, Paul Sulmon, and Christian Stevens. 1991. “Synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic Acids from Β-chloroaldimines.” Tetrahedron 47 (26): 4723–4738.
APA
De Kimpe, N., Sulmon, P., & Stevens, C. (1991). Synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids from β-chloroaldimines. TETRAHEDRON, 47(26), 4723–4738.
Vancouver
1.
De Kimpe N, Sulmon P, Stevens C. Synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids from β-chloroaldimines. TETRAHEDRON. 1991;47(26):4723–38.
MLA
De Kimpe, Norbert, Paul Sulmon, and Christian Stevens. “Synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic Acids from Β-chloroaldimines.” TETRAHEDRON 47.26 (1991): 4723–4738. Print.
@article{335517,
  abstract     = {A variety of hydrogen cyanide adducts of beta-chloroaldimines using acetone cyanohydrin were prepared. The reactive behaviour of these alpha-amino-gamma-chloronitriles towards bases was investigated with the aim to generate 1-aminocyclopropanecarbonitriles, which are precursors for the potentially plant growth regulating 1-aminocyclopropanecarboxylic acids. The synthesis of 1-amino-2,2-dimethylcyclopropanecarboxylic acid (= 2,3-methanovaline) by a reaction sequence involving addition of hydrogen cyanide across beta-chloroaldimines, ring closure to functionalized cyclopropanes and acidic hydrolysis was accomplished. Alternatively the hydrogen cyanide adducts of beta-chloroaldimines were converted into alpha-(N-benzylidene)amino-gamma-chloronitriles, which were ring closed with base and hydrolyzed to afford 1-amino-2,2-dialkylcyclopropanecarbonitriles, the latter serving again as substrates for the hydrolytic conversion into the corresponding 1-amino-2,2-dialkylcyclopropanecarboxylic acids (exemplified for 1-amino-2,2-dimethylcyclopropanecarboxylic acid).},
  author       = {De Kimpe, Norbert and Sulmon, Paul and Stevens, Christian},
  issn         = {0040-4020},
  journal      = {TETRAHEDRON},
  keyword      = {ALGA GRATELOUPIA-CARNOSA,CYCLOPROPANE AMINO-ACIDS,2,2-DIALKYL-1-AMINOCYCLOPROPANECARBOXYLIC ACIDS,ETHYLENE BIOSYNTHESIS,CHLOROIMINES,KETIMINES,CHEMISTRY,IMINES},
  language     = {eng},
  number       = {26},
  pages        = {4723--4738},
  title        = {Synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids from \ensuremath{\beta}-chloroaldimines},
  url          = {http://dx.doi.org/10.1016/S0040-4020(01)86477-2},
  volume       = {47},
  year         = {1991},
}

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