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Synlett 1991; 1991(11): 833-835
DOI: 10.1055/s-1991-20896
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Nucleophilic Reaction with Methyl Cyanoformate: A Novel α-Cyanomethylation and Hydrocyanation of α,β-Unsaturated Carbonyl Compounds

Takeshi Shimizu* , Sayoko Hiranuma, Satoshi Hayashibe, Hirosuke Yoshioka
  • *Riken (Institute of Physical and Chemical Research), Wako-shi, Saitama, 351-01, Japan
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Publication Date:
07 March 2002 (online)

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Methyl cyanoformate (1), well known as an electrophile in regioselective synthesis of β-keto esters from lithium enolates, reacted as a nucleophile with cyclic α-phenylthiomethyl α,β-unsaturated carbonyl compounds (II) to give α-cyanomethyl αβ-unsaturated carbonyl compounds (III) in high yields. Compound 1 also reacted with α,β-unsaturated carbonyl compounds (I) to give β-cyano ketones (IV).