Synthesis of Z,Z-Trishomofarnesal tert-butylimine

  • N. Ya. Grigor'eva
  • O. N. Yudina
  • O. A. Pinsker
  • E. D. Daeva
  • A. M. Moiseenkov
Organic Chemistry

Abstract

A highly stereoselective method was developed for the preparation of Z,Z-trishomofarnesal tert-butylimine, a key block synthone required for the construction of polyprenols with a nonnatural configuration of the “head” end of the chain, using as a basis the controlled condensation of aldehydes with aldimines. It was shown that introduction into the condensation of aldehydes containing an acetal grouping at the ω-position results in the formation of considerable amounts of aldols. The use of α-trimethylsilyl derivatives of aldimines makes it possible to dispense with this process and to direct the reaction toward the desired Eacroleins.

Keywords

Acetal Aldehyde Aldol Acetal Grouping Aldimines 

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Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • N. Ya. Grigor'eva
    • 1
  • O. N. Yudina
    • 1
  • O. A. Pinsker
    • 1
  • E. D. Daeva
    • 1
  • A. M. Moiseenkov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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