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Asymmetric addition of methyl nitroacetate to crotonaldehyde catalyzed by chiral amines

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The asymmetric Michael addition of methyl nitroacetate to crotonaldehyde catalyzed by chiral amines was carried out. The maximum chemical yield of diastereomeric products amounted to 95 %. The best asymmetric induction (42 % e.e.) was achieved in the case of catalysis by (S)-prolinol. The diastereomeric mixture was converted to a mixture of stereoisomeric 3-methyl-2-methoxycarbonylpyrrolidines. Absolute configurations of (2S,3S)-and (2R,3S)-isomers formed in excess were determined using GLC by comparison with authentic samples of racemic and optically pure forms of 3-methylproline.

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1591–1595, September, 1993.

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Belokon', Y.N., Kochetkov, K.A., Churkina, T.D. et al. Asymmetric addition of methyl nitroacetate to crotonaldehyde catalyzed by chiral amines. Russ Chem Bull 42, 1525–1529 (1993).

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Key words

  • asymmetric Michael addition
  • chiral amines
  • catalysis
  • methyl nitroacetate
  • crotonaldehyde
  • (S)-prolinol
  • 3-methylproline, enantiomeric excess