Syntheses of α-Alkylated β, γ-Unsaturated α-Amino Acids

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概要

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• Various α-alkylated β, γ-unsaturated α-amino acids were synthesized by the deconjugative alkylation of methyl α-isocyanoalkylideneacetates followed by hydrolysis. In the mechanistic study, no marked differences in reactivity of the geometrical isomers of methyl 2-isocyano-3-phenyl-2-butenoate (E-and Z-11a) were observed. On the other hand, the double bound migration of unsymmetrical (R^1≠R^2) isocyano compounds (11c, d) proceeded regioselectively due both to the different acidities of the alkyl groups and to the stability of the carbanion formed on proton abstraction. Furthermore, direct synthesis of methyl α-isocyanocycloalkylideneacetates (4a, b, d) by the reaction of methyl isocyanoacetate with cyclic ketones was also investigated.

• 1982-11-25

著者

• 鈴木 護

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.,

• 沼波 憲一

  生化研

• 米田 直人

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

• 沼波 憲一

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

• 米田 直人

  Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.

• 鈴木 護

  Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.

• 米田 直人

  Research Laboratory of Applied Biochemistry

• 米田 直人

  Research Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.

• 沼波 憲一

  Research Laboratory of Applied Biochemistry

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