Russian Chemical Bulletin

, Volume 61, Issue 8, pp 1616–1621 | Cite as

Preparation of (2E,4E)-2-(2-benzyloxyethyl)-5-(3-methoxy-4-chlorophenyl)penta-2,4-dienal as a key intermediate in the synthesis of strobilurin B

  • V. A. Popovsky
  • A. V. Stepanov
  • N. Ya. Grigorieva
Full Articles


(2E,4E)-2-(2-Benzyloxyethyl)-5-(4-chloro-3-methoxyphenyl)penta-2,4-dienal was obtained by the condensation of 4-benzyloxybutanal N-tert-butylimine with 4-chloro-3-methoxycinnamic aldehyde with ≥98% configurational purity and 40% yield. When 4-benzyloxy-2-triethylsilylbutanal imine was used, a 7: 3 mixture of the target (2E,4E)-dienal with its (2Z,4E)-isomer was obtained in 60% yield; the latter quantitatively isomerized to the thermodynamically preferable target (2E,4E)-dienal.

Key words

strobilurins aldol condensation stereocontrolled synthesis aldimines arylenals dienals 


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Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • V. A. Popovsky
    • 1
  • A. V. Stepanov
    • 1
  • N. Ya. Grigorieva
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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