Bulletin of the Chemical Society of Japan p. 2107 - 2112 (1981)
Update date:2022-09-26
Topics:
Kurihara, Toshio
Sugizaki, Masaru
Kime, Itaru
Wada, Makoto
Mitsunobu, Oyo
The reagent formed by the reaction of diethyl azodicarboxylate (1) and triphenylphosphine (2) reacted with alcohols and ethyl cyanoacetate (6) to give alkylated products in 30 - 80percent yields.When ethyl acetoacetate, 1,3-1,3-coclopentanedione, or 1,3-cyclohexanedione was used in place of 6, the corresponding O-alkylated products were obtained.The reaction of either (S)-(-)-ethyl lactate or (S)-(-)-ethyl 2-hydroxy-3-phenylpropionate with 1, 2, and 6, followed by hydrolysis resulted in the formation of (S)-(-)-methylsuccinic acid or (S)-(-)-benzylsuccinic acid.The results indicate that nearly complete inversion of the configuration takes place in the alkylation step.
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